RXNO is the name reaction ontology. It contains more than 500 classes representing organic reactions such as the Diels–Alder cyclization. RXNO 16:12:2021 15:55 RXNO 1.2 definition has_alternative_id has_broad_synonym database_cross_reference has_exact_synonym has_narrow_synonym has_obo_format_version has_obo_namespace has_related_synonym has_synonym_type in_subset RXNO part_of part_of RXNO BFO:0000015 process BFO:0000015 RXNO BFO:0000016 disposition BFO:0000016 true CHEBI:13281 true CHEBI:13368 true CHEBI:13382 true CHEBI:13388 true CHEBI:13405 true CHEBI:13406 true CHEBI:13407 true CHEBI:13435 true CHEBI:13443 true CHEBI:13444 true CHEBI:13694 true CHEBI:13696 RXNO CHEBI:13759 alkylamine CHEBI:13759 true CHEBI:13771 An alpha-oxyketone that has a hydroxy group as the alpha-oxy moiety. http://purl.obolibrary.org/obo/chebi/205/chebi.owl chebi_ontology CHEBI:139588 alpha-hydroxy ketone CHEBI:139588 true CHEBI:14137 true CHEBI:14660 true CHEBI:14777 RXNO CHEBI:15379 dioxygen CHEBI:15379 RXNO CHEBI:15734 primary alcohol CHEBI:15734 An organic hydroxy compound that consists of benzene bearing a single hydroxy substituent. The parent of the class of phenols. http://purl.obolibrary.org/obo/chebi/206/chebi.owl CHEBI:14777 CHEBI:25966 CHEBI:43543 CHEBI:8071 chebi_ontology CHEBI:15882 phenol CHEBI:15882 An azane that consists of a single nitrogen atom covelently bonded to three hydrogen atoms. http://purl.obolibrary.org/obo/chebi/206/chebi.owl CHEBI:13405 CHEBI:13406 CHEBI:13407 CHEBI:13771 CHEBI:22533 CHEBI:44269 CHEBI:44284 CHEBI:44404 CHEBI:7434 chebi_ontology CHEBI:16134 ammonia CHEBI:16134 RXNO CHEBI:16227 pyridine CHEBI:16227 RXNO CHEBI:16240 hydrogen peroxide CHEBI:16240 Compounds having the structure RSR (R =/= H). Such compounds were once called thioethers. CHEBI:13694 CHEBI:26960 CHEBI:9340 chebi_ontology CHEBI:16385 organic sulfide CHEBI:16385 RXNO CHEBI:16526 carbon dioxide CHEBI:16526 http://purl.obolibrary.org/obo/chebi/206/chebi.owl CHEBI:14137 CHEBI:23664 CHEBI:4486 chebi_ontology CHEBI:16648 dialkyl phosphate CHEBI:16648 RXNO CHEBI:16670 peptide CHEBI:16670 RXNO CHEBI:16842 formaldehyde CHEBI:16842 RXNO CHEBI:17087 ketone CHEBI:17087 A one-carbon compound in which the carbon is joined only to a single oxygen. It is a colourless, odourless, tasteless, toxic gas. http://purl.obolibrary.org/obo/chebi/206/chebi.owl CHEBI:13281 CHEBI:23013 CHEBI:3282 CHEBI:41526 chebi_ontology CHEBI:17245 carbon monoxide CHEBI:17245 An organosilicon compound that is benzene in which a hydrogen is replaced by a silyl group. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:172874 phenylsilane CHEBI:172874 true CHEBI:17366 RXNO CHEBI:17478 aldehyde CHEBI:17478 A compound containing at least one carbon-halogen bond (where X is a halogen atom). http://purl.obolibrary.org/obo/chebi/206/chebi.owl CHEBI:13444 CHEBI:36684 CHEBI:8767 chebi_ontology CHEBI:17792 organohalogen compound CHEBI:17792 RXNO CHEBI:17883 hydrogen chloride CHEBI:17883 An elemental molecule consisting of two trivalently-bonded nitrogen atoms. 0 N2 InChI=1S/N2/c1-2 IJGRMHOSHXDMSA-UHFFFAOYSA-N 28.01348 28.00615 N#N CHEBI:13388 CHEBI:14660 CHEBI:25365 CHEBI:43128 CHEBI:7593 CAS:7727-37-9 Drug_Central:4251 Gmelin:150 HMDB:HMDB0001371 KEGG:C00697 KEGG:D00083 MetaCyc:NITROGEN-MOLECULE PDBeChem:HDZ PMID:18334638 PMID:22237545 Reaxys:15940095 Wikipedia:Nitrogen dinitrogen chebi_ontology N#N N2 Nitrogen molecular nitrogen CHEBI:17997 dinitrogen CHEBI:17997 CAS:7727-37-9 ChemIDplus N#N ChEBI N2 IUPAC N2 KEGG_COMPOUND N2 UniProt Nitrogen KEGG_COMPOUND molecular nitrogen ChEBI CAS:7727-37-9 KEGG COMPOUND CAS:7727-37-9 NIST Chemistry WebBook Drug_Central:4251 DrugCentral Gmelin:150 Gmelin PMID:18334638 Europe PMC PMID:22237545 Europe PMC Reaxys:15940095 Reaxys dinitrogen IUPAC http://purl.obolibrary.org/obo/chebi/206/chebi.owl CHEBI:13368 CHEBI:37140 CHEBI:5599 chebi_ontology CHEBI:18140 hydrogen halide CHEBI:18140 A manganese group element atom that has formula Mn. http://purl.obolibrary.org/obo/chebi/206/chebi.owl CHEBI:13382 CHEBI:25153 CHEBI:6681 chebi_ontology CHEBI:18291 manganese atom CHEBI:18291 An acyclic branched or unbranched hydrocarbon having the general formula CnH2n+2, and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. 0 CH3R 15.035 15.02348 C[*] CHEBI:13435 CHEBI:22317 CHEBI:2576 KEGG:C01371 Alkane alkane alkanes chebi_ontology Alkan RH alcane alcanes alcano alcanos an alkane CHEBI:18310 alkane CHEBI:18310 Alkane KEGG_COMPOUND alkane IUPAC alkanes IUPAC Alkan ChEBI RH KEGG_COMPOUND alcane IUPAC alcanes IUPAC alcano IUPAC alcanos IUPAC an alkane UniProt RXNO CHEBI:18379 nitrile CHEBI:18379 RXNO CHEBI:22213 acridines CHEBI:22213 true CHEBI:22317 http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:22324 alkyl phosphate CHEBI:22324 Acyclic branched or unbranched hydrocarbons having a carbon-carbon triple bond and the general formula CnH2n-2, RC#CR. chebi_ontology CHEBI:22339 alkyne CHEBI:22339 RXNO CHEBI:22495 CHEBI:33855 arenecarbaldehyde CHEBI:22495 true CHEBI:22533 RXNO CHEBI:22680 azide CHEBI:22680 RXNO CHEBI:22698 benzaldehydes CHEBI:22698 Any benzenoid aromatic compound consisting of the benzene skeleton and its substituted derivatives. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:22712 benzenes CHEBI:22712 RXNO CHEBI:22715 benzimidazoles CHEBI:22715 RXNO CHEBI:22929 bromoalkane CHEBI:22929 true CHEBI:23013 http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:23014 carbon oxide CHEBI:23014 0 CO 28.01010 27.99491 O=C(*)* carbonyl carbonyl group chebi_ontology >C=O CHEBI:23019 carbonyl group CHEBI:23019 carbonyl IUPAC carbonyl group ChEBI carbonyl group UniProt >C=O IUPAC RXNO CHEBI:23086 chalcones CHEBI:23086 RXNO CHEBI:23128 chloroalkane CHEBI:23128 RXNO CHEBI:23252 cinnamic acids CHEBI:23252 RXNO CHEBI:23367 molecular entity CHEBI:23367 Salts and C-organyl derivatives of hydrogen cyanide, HC#N. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:23424 cyanides CHEBI:23424 true CHEBI:23664 true CHEBI:23960 RXNO CHEBI:24043 flavones CHEBI:24043 RXNO CHEBI:24079 formamides CHEBI:24079 RXNO CHEBI:24129 furans CHEBI:24129 RXNO CHEBI:24431 chemical entity CHEBI:24431 RXNO CHEBI:24433 group CHEBI:24433 RXNO CHEBI:24469 haloalkane CHEBI:24469 A compound derived from a hydrocarbon by replacing a hydrogen atom with a halogen atom. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:24472 halohydrocarbon CHEBI:24472 true CHEBI:24671 RXNO CHEBI:24828 indoles CHEBI:24828 RXNO CHEBI:25000 lactone CHEBI:25000 true CHEBI:25153 true CHEBI:25365 true CHEBI:25429 Any member of the class of toluenes bearing one or more nitro substituents on the benzene ring. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:25566 nitrotoluene CHEBI:25566 RXNO CHEBI:25698 ether CHEBI:25698 http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:25703 organic phosphate CHEBI:25703 A compound having bonds between one or more metal atoms and one or more carbon atoms of an organyl group. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:25707 organometallic compound CHEBI:25707 RXNO CHEBI:25710 organophosphorus compound CHEBI:25710 An organosilicon compound is a compound containing at least one carbon-silicon bond. organosilicon compound chebi_ontology organosilicon compounds silicoorganic compounds CHEBI:25713 organosilicon compound CHEBI:25713 organosilicon compound ChEBI organosilicon compounds ChEBI silicoorganic compounds ChEBI RXNO CHEBI:25717 organotin compound CHEBI:25717 RXNO CHEBI:25750 oxime CHEBI:25750 true CHEBI:2576 true CHEBI:2591 true CHEBI:25966 RXNO CHEBI:25996 phenylhydrazine CHEBI:25996 true CHEBI:26068 Derivatives of oxoacids RnE(=O)OH in which the hydroxy group is replaced by an amino group and the oxo group is replaced by =NR. In organic chemistry an unspecified amidine is commonly a carboxamidine. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:2634 amidine CHEBI:2634 http://purl.obolibrary.org/obo/chebi/205/chebi.owl chebi_ontology CHEBI:26407 pyrans CHEBI:26407 RXNO CHEBI:26410 pyrazoles CHEBI:26410 RXNO CHEBI:26421 pyridines CHEBI:26421 RXNO CHEBI:26455 pyrroles CHEBI:26455 RXNO CHEBI:26513 quinolines CHEBI:26513 A molecular entity possessing an unpaired electron. http://purl.obolibrary.org/obo/chebi/205/chebi.owl chebi_ontology CHEBI:26519 radical CHEBI:26519 RXNO CHEBI:26588 triazines CHEBI:26588 RXNO CHEBI:26708 sodium atom CHEBI:26708 RXNO CHEBI:26878 tertiary alcohol CHEBI:26878 true CHEBI:26960 RXNO CHEBI:26961 thiophenes CHEBI:26961 true CHEBI:26969 Any member of the class of benzenes that is a substituted benzene in which the substituents include one (and only one) methyl group. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:27024 toluenes CHEBI:27024 RXNO CHEBI:27081 transition element atom CHEBI:27081 RXNO CHEBI:27363 zinc atom CHEBI:27363 RXNO CHEBI:27385 tetrachloromethane CHEBI:27385 RXNO CHEBI:27539 isatin CHEBI:27539 RXNO CHEBI:278547 sodium azide CHEBI:278547 RXNO CHEBI:28112 nickel atom CHEBI:28112 RXNO CHEBI:28659 phosphorus atom CHEBI:28659 RXNO CHEBI:28694 copper atom CHEBI:28694 RXNO CHEBI:28802 flavonols CHEBI:28802 RXNO CHEBI:29224 dibromine CHEBI:29224 An organosulfur compound in which a thiol group, -SH, is attached to a carbon atom of any aliphatic or aromatic moiety. CHEBI:13443 CHEBI:13696 CHEBI:17366 CHEBI:26969 CHEBI:8766 CHEBI:9556 chebi_ontology CHEBI:29256 thiol CHEBI:29256 A sulfur hydride that has formula HS. chebi_ontology CHEBI:29312 sulfanyl CHEBI:29312 RXNO CHEBI:29785 nitro group CHEBI:29785 0 H2N2 InChI=1S/H2N2/c1-2/h1-2H RAABOESOVLLHRU-UHFFFAOYSA-N 30.02936 30.02180 N=N CAS:3618-05-1 KEGG:C05360 diazene chebi_ontology Diimide HN=NH CHEBI:30096 diazene CHEBI:30096 CAS:3618-05-1 ChemIDplus CAS:3618-05-1 NIST Chemistry WebBook diazene IUPAC Diimide NIST_Chemistry_WebBook HN=NH IUPAC RXNO CHEBI:30879 alcohol CHEBI:30879 An indolinone carrying an oxo group at position 2. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:31697 indolin-2-one CHEBI:31697 RXNO CHEBI:32816 pyruvic acid CHEBI:32816 true CHEBI:3282 RXNO CHEBI:32863 secondary amine CHEBI:32863 RXNO CHEBI:32876 tertiary amine CHEBI:32876 RXNO CHEBI:32877 primary amine CHEBI:32877 RXNO CHEBI:32878 alkene CHEBI:32878 RXNO CHEBI:32952 amine CHEBI:32952 RXNO CHEBI:32955 epoxide CHEBI:32955 RXNO CHEBI:32988 amide CHEBI:32988 RXNO CHEBI:33250 atom CHEBI:33250 RXNO CHEBI:33256 primary amide CHEBI:33256 A molecular entity all atoms of which have the same atomic number. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:33259 elemental molecular entity CHEBI:33259 RXNO CHEBI:33308 carboxylic ester CHEBI:33308 RXNO CHEBI:33338 aryl group CHEBI:33338 RXNO CHEBI:33341 titanium atom CHEBI:33341 RXNO CHEBI:33363 palladium atom CHEBI:33363 RXNO CHEBI:33364 platinum atom CHEBI:33364 http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:33403 elemental sulfur CHEBI:33403 http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:33434 elemental halogen CHEBI:33434 RXNO CHEBI:33521 metal atom CHEBI:33521 RXNO CHEBI:33575 carboxylic acid CHEBI:33575 RXNO CHEBI:33595 cyclic compound CHEBI:33595 A cyclic compound having as ring members atoms of the same element only. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:33597 homocyclic compound CHEBI:33597 A homocyclic compound in which all of the ring members are carbon atoms. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:33598 carbocyclic compound CHEBI:33598 http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:33635 polycyclic compound CHEBI:33635 RXNO CHEBI:33641 olefin CHEBI:33641 A cyclically conjugated molecular entity with a stability (due to delocalization) significantly greater than that of a hypothetical localized structure (e.g. Kekule structure) is said to possess aromatic character. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:33655 aromatic compound CHEBI:33655 RXNO CHEBI:33658 arene CHEBI:33658 http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:33659 organic aromatic compound CHEBI:33659 A polycyclic compound in which at least one of the rings contains at least one non-carbon atom. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:33671 heteropolycyclic compound CHEBI:33671 RXNO CHEBI:33822 organic hydroxy compound CHEBI:33822 RXNO CHEBI:33823 enol CHEBI:33823 http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:33836 benzenoid aromatic compound CHEBI:33836 RXNO CHEBI:33839 macromolecule CHEBI:33839 A monocyclic aromatic hydrocarbon. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:33847 monocyclic arene CHEBI:33847 A polycyclic aromatic hydrocarbon. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:33848 polycyclic arene CHEBI:33848 RXNO CHEBI:33853 phenols CHEBI:33853 RXNO CHEBI:33860 aromatic amine CHEBI:33860 RXNO CHEBI:35255 chloroform CHEBI:35255 RXNO CHEBI:35293 fused compound CHEBI:35293 RXNO CHEBI:35352 organonitrogen compound CHEBI:35352 The isomer HN(+)#C(-) of hydrocyanic acid, HC#N, and its hydrocarbyl derivatives RNC (RN(+)#C(-)). http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:35353 isocyanide CHEBI:35353 RXNO CHEBI:35403 chromium coordination entity CHEBI:35403 RXNO CHEBI:35562 1,2,3-triazole CHEBI:35562 RXNO CHEBI:35636 carboximides CHEBI:35636 RXNO CHEBI:35681 secondary alcohol CHEBI:35681 RXNO CHEBI:35689 tetrazoles CHEBI:35689 A compound formally derived from an oxoacid RkE(=O)l(OH)m (l > 0) and an alcohol, phenol, heteroarenol, or enol by linking with formal loss of water from an acidic hydroxy group of the former and a hydroxy group of the latter. http://purl.obolibrary.org/obo/chebi/206/chebi.owl CHEBI:23960 CHEBI:4859 chebi_ontology CHEBI:35701 ester CHEBI:35701 RXNO CHEBI:35715 nitro compound CHEBI:35715 RXNO CHEBI:35873 carboxylic anhydride CHEBI:35873 RXNO CHEBI:35886 tertiary phosphine CHEBI:35886 RXNO CHEBI:36587 carbonyl compound CHEBI:36587 RXNO CHEBI:36601 triphenylphosphane oxide CHEBI:36601 RXNO CHEBI:36605 phthalic anhydride CHEBI:36605 RXNO CHEBI:36606 acid anhydride CHEBI:36606 true CHEBI:36684 RXNO CHEBI:36687 acyl chloride CHEBI:36687 RXNO CHEBI:36823 pseudohalo group CHEBI:36823 http://purl.obolibrary.org/obo/chebi/205/chebi.owl chebi_ontology CHEBI:36871 inorganic radical CHEBI:36871 http://purl.obolibrary.org/obo/chebi/205/chebi.owl chebi_ontology CHEBI:36872 organic radical CHEBI:36872 RXNO CHEBI:36963 organooxygen compound CHEBI:36963 true CHEBI:37140 RXNO CHEBI:37148 bromoarene CHEBI:37148 Any heteroatomic molecular entity that is a chemical compound of halogen with other chemical elements. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:37578 halide CHEBI:37578 RXNO CHEBI:37579 acyl halide CHEBI:37579 RXNO CHEBI:37592 organic phosphonate CHEBI:37592 RXNO CHEBI:37602 allenes CHEBI:37602 RXNO CHEBI:37613 cyclohexadiene CHEBI:37613 RXNO CHEBI:37622 carboxamide CHEBI:37622 A phosphonic acid derivative in which one or both OH groups have been esterified. http://purl.obolibrary.org/obo/chebi/206/chebi.owl CHEBI:26068 CHEBI:4861 chebi_ontology CHEBI:37735 phosphonic ester CHEBI:37735 RXNO CHEBI:37757 iodoalkane CHEBI:37757 Any of a class of cyclic chemical compounds that contain an unsaturated six-membered ring with one ring oxygen atom and an oxo substituent. http://purl.obolibrary.org/obo/chebi/205/chebi.owl chebi_ontology CHEBI:37963 pyranone CHEBI:37963 true CHEBI:38075 Any organonitrogen compound containing a cyclic component with nitrogen and at least one other element as ring member atoms. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:38101 organonitrogen heterocyclic compound CHEBI:38101 RXNO CHEBI:38104 oxacycle CHEBI:38104 thiacycle RXNO CHEBI:38106 I think this is the same as a thiacycle but need to check. organosulfur heterocyclic compound CHEBI:38106 http://purl.obolibrary.org/obo/chebi/206/chebi.owl CHEBI:25429 CHEBI:38075 chebi_ontology CHEBI:38166 organic heteropolycyclic compound CHEBI:38166 RXNO CHEBI:38269 boronic acids CHEBI:38269 RXNO CHEBI:38597 triazole CHEBI:38597 RXNO CHEBI:38757 isoflavones CHEBI:38757 RXNO CHEBI:38784 oxetanes CHEBI:38784 A monocyclic arene that is benzene substituted with one or more alkyl groups. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:38976 alkylbenzene CHEBI:38976 RXNO CHEBI:39141 Brønsted acid CHEBI:39141 RXNO CHEBI:39142 Brønsted base CHEBI:39142 RXNO CHEBI:39143 Lewis acid CHEBI:39143 RXNO CHEBI:39144 Lewis base CHEBI:39144 A haloalkane that is methane in which one (or more) of the hydrogens have been replaced by a halogen atom/halogen atoms. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:39279 halomethane CHEBI:39279 RXNO CHEBI:39447 pyrimidines CHEBI:39447 Radicals derived from hydroxylamines by removal of the hydrogen atom from the hydroxy group. The synonymous terms nitroxyl radicals and nitroxides erroneously suggest the presence of a nitro group. http://purl.obolibrary.org/obo/chebi/205/chebi.owl chebi_ontology CHEBI:39477 aminoxyls CHEBI:39477 true CHEBI:41526 RXNO CHEBI:42485 formyl group CHEBI:42485 true CHEBI:43128 RXNO CHEBI:43176 hydroxy group CHEBI:43176 true CHEBI:43543 true CHEBI:44269 true CHEBI:44284 true CHEBI:44404 true CHEBI:4486 A dithiol that is propane substituted by thiol groups at positions 1 ans 3. http://purl.obolibrary.org/obo/chebi/200/chebi.owl chebi_ontology CHEBI:44864 propane-1,3-dithiol CHEBI:44864 RXNO CHEBI:46882 amino group CHEBI:46882 RXNO CHEBI:46883 carboxy group CHEBI:46883 RXNO CHEBI:47266 hydrogen bromide CHEBI:47266 RXNO CHEBI:47875 tetrabromomethane CHEBI:47875 Ethers ROR' where R has a double bond adjacent to the oxygen of the ether linkage. http://purl.obolibrary.org/obo/chebi/205/chebi.owl chebi_ontology CHEBI:47985 enol ether CHEBI:47985 Enol ethers ROR' where R' has the structure SiR''R'''R''''. http://purl.obolibrary.org/obo/chebi/205/chebi.owl chebi_ontology CHEBI:47986 silyl enol ether CHEBI:47986 Ethers ROR' where R' has the structure SiR''R'''R''''. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:47988 silyl ether CHEBI:47988 RXNO CHEBI:48420 chromium trioxide CHEBI:48420 RXNO CHEBI:48513 carbazoles CHEBI:48513 true CHEBI:4859 true CHEBI:4861 An azole in which the five-membered heterocyclic aromatic skeleton contains a N atom and one S atom. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:48901 thiazoles CHEBI:48901 RXNO CHEBI:49553 copper(II) chloride CHEBI:49553 A compound formally derived from ammonia by replacing one, two or three hydrogen atoms by organyl groups. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:50047 organic amino compound CHEBI:50047 RXNO CHEBI:50075 dihydropyridine CHEBI:50075 http://purl.obolibrary.org/obo/chebi/205/chebi.owl CHEBI:24671 CHEBI:5798 chebi_ontology CHEBI:50413 hydroxyaldehyde CHEBI:50413 RXNO CHEBI:50784 pivalate ester CHEBI:50784 A compound derived from an arene by replacing a hydrogen atom with a halogen atom. http://purl.obolibrary.org/obo/chebi/200/chebi.owl chebi_ontology CHEBI:50887 haloarene CHEBI:50887 RXNO CHEBI:50888 fluoroarene CHEBI:50888 A salt or ester of boronic acid. http://purl.obolibrary.org/obo/chebi/200/chebi.owl chebi_ontology CHEBI:50978 boronate CHEBI:50978 RXNO CHEBI:51080 nitrate ester CHEBI:51080 RXNO CHEBI:51142 amino groups CHEBI:51142 RXNO CHEBI:51154 phosphonium ylide CHEBI:51154 A compound containing at least one carbon-lithium bond. http://purl.obolibrary.org/obo/chebi/200/chebi.owl chebi_ontology CHEBI:51186 organolithium compound CHEBI:51186 A compound containing at least one carbon-magnesium bond. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:51187 organomagnesium compound CHEBI:51187 RXNO CHEBI:51236 organomagnesium halide CHEBI:51236 A compound of general formula RC(=O)SR'. Compare with thionoester, RC(=S)OR'. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:51277 thioester CHEBI:51277 RXNO CHEBI:51454 cyclopropanes CHEBI:51454 An organolithium compound where an alkyl group is bound to a lithium atom. http://purl.obolibrary.org/obo/chebi/200/chebi.owl chebi_ontology CHEBI:51462 alkyllithium compound CHEBI:51462 An alkyllithium compound that has formula C4H9Li. http://purl.obolibrary.org/obo/chebi/200/chebi.owl chebi_ontology CHEBI:51469 butyllithium CHEBI:51469 A compound containing at least one carbon-zinc bond. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:51494 organozinc compound CHEBI:51494 Any compound containing two aryl groups connected by a single C atom. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:51614 diarylmethane CHEBI:51614 RXNO CHEBI:51721 alpha,beta-unsaturated ketone CHEBI:51721 A haloketone in which the halogen and oxo substituents are on adjacent carbon atoms. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:51839 alpha-haloketone CHEBI:51839 RXNO CHEBI:51849 beta-ketoester CHEBI:51849 A ketone of formula RC(=O)CH3 (R =/= H). http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:51867 methyl ketone CHEBI:51867 RXNO CHEBI:51929 arylacetylene CHEBI:51929 RXNO CHEBI:52094 peroxy acid CHEBI:52094 A compound with the general formula R2C=O (R=/=H) where one or more of the R groups contains an oxy (-O-) group. http://purl.obolibrary.org/obo/chebi/205/chebi.owl chebi_ontology CHEBI:52395 oxyketone CHEBI:52395 RXNO CHEBI:53212 isocyanates CHEBI:53212 RXNO CHEBI:53434 palladium(II) chloride CHEBI:53434 RXNO CHEBI:55380 beta-hydroxy ketone CHEBI:55380 true CHEBI:5599 A compound having the general formula RR'C(OH)OR'' (R'' =/= H). 0 CH2O2R2 46.025 46.00548 Hemiacetal hemiacetals chebi_ontology hemiacetals CHEBI:5653 hemiacetal CHEBI:5653 Hemiacetal KEGG_COMPOUND hemiacetals IUPAC hemiacetals ChEBI RXNO CHEBI:5686 heterocyclic compound CHEBI:5686 true CHEBI:5798 RXNO CHEBI:59656 phosphine oxide CHEBI:59656 An organooxygen compound having the structure RR'C(OR'')(OR''') (R'', R''' =/= H). Mixed acetals have R'' and R''' groups which differ. chebi_ontology acetals CHEBI:59769 acetal CHEBI:59769 acetals ChEBI RXNO CHEBI:59831 enyne CHEBI:59831 A chemical substance is a portion of matter of constant composition, composed of molecular entities of the same type or of different types. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:59999 chemical substance CHEBI:59999 A mixture is a chemical substance composed of multiple molecules, at least two of which are of a different kind. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:60004 mixture CHEBI:60004 A polymer is a mixture, which is composed of macromolecules of different kinds and which may be differentiated by composition, length, degree of branching etc.. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:60027 polymer CHEBI:60027 An organic phosphonate containing a C-PO(OH)2 or C-PO(OR)2 group (where R = alkyl group). http://purl.obolibrary.org/obo/chebi/206/chebi.owl CHEBI:2591 chebi_ontology CHEBI:60983 alkylphosphonate CHEBI:60983 An organic phosphonate of formula (RO)2P(=O)-CR2-NR2; R can be H. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:61111 aminophosphonate CHEBI:61111 true CHEBI:6681 Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen. http://purl.obolibrary.org/obo/chebi/206/chebi.owl chebi_ontology CHEBI:68452 azole CHEBI:68452 RXNO CHEBI:72695 organic molecule CHEBI:72695 RXNO CHEBI:73474 acetylenic compound CHEBI:73474 RXNO CHEBI:73477 terminal acetylenic compound CHEBI:73477 true CHEBI:7434 true CHEBI:7593 true CHEBI:8071 true CHEBI:8766 true CHEBI:8767 true CHEBI:9340 true CHEBI:9556 RXNO IAO:0000005 objective specification IAO:0000005 RXNO IAO:0000030 information content entity IAO:0000030 Formation of a covalent bond between a substrate and a formyl group. formylation RXNO MOP:0000003 formylation MOP:0000003 Formation of a covalent bond between a substrate and a formyl group. RSC:xp Formation of a covalent bond between a substrate and an silyl group. silylation RXNO MOP:0000339 has_participant: CHEBI:33478 silylation MOP:0000339 Formation of a covalent bond between a substrate and an silyl group. RSC:xp RXNO MOP:0000364 methylation MOP:0000364 Formation of a covalent bond between a substrate and an alkyl group. alkylation RXNO MOP:0000369 has_participant: CHEBI:22323 alkylation MOP:0000369 Formation of a covalent bond between a substrate and an alkyl group. RSC:xp Formation of a covalent bond between a substrate and a hydrocarbyl group. hydrocarbylation RXNO MOP:0000410 has_participant: CHEBI:33248 hydrocarbylation MOP:0000410 Formation of a covalent bond between a substrate and a hydrocarbyl group. RSC:xp Formation of a covalent bond between a substrate and an aryl group. arylation RXNO MOP:0000411 arylation MOP:0000411 Formation of a covalent bond between a substrate and an aryl group. RSC:xp Formation of a covalent bond between a substrate and an allyl group. allylation RXNO MOP:0000422 has_participant: CHEBI:30361 allylation MOP:0000422 Formation of a covalent bond between a substrate and an allyl group. RSC:xp Formation of a covalent bond between a substrate and an organyl group. organylation RXNO MOP:0000458 has_participant: CHEBI:33249 organylation MOP:0000458 Formation of a covalent bond between a substrate and an organyl group. RSC:xp Formation of a covalent bond between a substrate and an acyl group. acylation RXNO MOP:0000479 has_participant: CHEBI:22221 acylation MOP:0000479 Formation of a covalent bond between a substrate and an acyl group. RSC:xp true MOP:0000524 Formation of a covalent bond between a substrate and a sulfonyl group. MOP:0000524 sulfonylation RXNO MOP:0000539 has_participant: CHEBI:51100; has_participant: CHEBI:29825 sulfonylation MOP:0000539 Formation of a covalent bond between a substrate and a sulfonyl group. RSC:xp A process in which at least one of the participants is a molecule. RXNO MOP:0000543 TODO: needs work, formal definition, etc. molecular process MOP:0000543 A process in which at least one of the participants is a molecule. https://orcid.org/0000-0001-5985-7429 Formation of a covalent bond between a substrate and a halo group. RXNO MOP:0000550 has_participant: CHEBI:47854 halogenation MOP:0000550 Formation of a covalent bond between a substrate and a halo group. RSC:xp Formation of a covalent bond between a substrate and an imino group. RXNO MOP:0000555 has_participant: CHEBI:29342 imination MOP:0000555 Formation of a covalent bond between a substrate and an imino group. RSC:xp Formation of a covalent bond between a substrate and a nitro group. RXNO MOP:0000556 nitration MOP:0000556 Formation of a covalent bond between a substrate and a nitro group. RSC:xp Formation of a ring in a molecule from a chain by formation of a new bond. cyclisation RXNO MOP:0000561 cyclization MOP:0000561 Formation of a ring in a molecule from a chain by formation of a new bond. AU:C01494 A molecular process where two or more unsaturated molecules or parts of the same molecule combine to form a cyclic adduct in which there is a net reduction of bond multiplicity. RXNO:0000314 RXNO MOP:0000562 cycloaddition MOP:0000562 A molecular process where two or more unsaturated molecules or parts of the same molecule combine to form a cyclic adduct in which there is a net reduction of bond multiplicity. AU:C01496 A cycloaddition in which each participant contributes two electrons to the transformation of reactants to products. RXNO MOP:0000563 [2+2] cycloaddition MOP:0000563 A cycloaddition in which each participant contributes two electrons to the transformation of reactants to products. https://orcid.org/0000-0001-5985-7429 A molecular process in which a cyclic system decomposes into two or more unsaturated molecules or parts of the same molecule and there is a net increase in bond multiplicity. cycloreversion retro-addition retrocycloaddition RXNO MOP:0000564 cycloelimination MOP:0000564 A molecular process in which a cyclic system decomposes into two or more unsaturated molecules or parts of the same molecule and there is a net increase in bond multiplicity. AU:C01496 AU:C01501 cycloreversion AU:C01506 retrocycloaddition AU:R05372 A cycloaddition in which one participant contributes four electrons and the other participant contributes two electrons to the transformation of reactants to products. RXNO MOP:0000565 [4+2] cycloaddition MOP:0000565 A cycloaddition in which one participant contributes four electrons and the other participant contributes two electrons to the transformation of reactants to products. https://orcid.org/0000-0001-5985-7429 Formation of a covalent bond between a substrate and a group. batchelorc 2009-04-22T10:01:32Z RXNO MOP:0000566 formation of covalent bond with group MOP:0000566 Formation of a covalent bond between a substrate and a group. https://orcid.org/0000-0001-5985-7429 Breaking of a covalent bond between a substrate and a group. batchelorc 2009-04-30T02:24:32Z RXNO MOP:0000567 breaking of covalent bond with group MOP:0000567 Breaking of a covalent bond between a substrate and a group. https://orcid.org/0000-0001-5985-7429 The complete, net removal of one or mole electrons from a molecular entity, corresponding to an increase in the oxidation number of any atom within any substrate. batchelorc 2009-06-01T06:01:47Z de-electronation RXNO MOP:0000568 oxidation MOP:0000568 The complete, net removal of one or mole electrons from a molecular entity, corresponding to an increase in the oxidation number of any atom within any substrate. AU:O04362 The complete transfer of one or more electrons to a molecular entity. batchelorc 2009-06-01T06:04:18Z electronation RXNO MOP:0000569 reduction MOP:0000569 The complete transfer of one or more electrons to a molecular entity. AU:R05222 The transfer of an electron to a molecular entity, resulting in a molecular entity of increased negative charge. batchelorc 2009-06-01T06:06:19Z RXNO MOP:0000570 electron attachment MOP:0000570 The transfer of an electron to a molecular entity, resulting in a molecular entity of increased negative charge. AU:E01979 A reduction in which an aldehyde is reduced to form a primary alcohol. batchelorc 2009-06-01T06:07:02Z RXNO MOP:0000571 aldehyde reduction MOP:0000571 A reduction in which an aldehyde is reduced to form a primary alcohol. https://orcid.org/0000-0001-5985-7429 An oxidation process where an alcohol is transformed into a carbonyl compound. batchelorc 2009-06-01T06:10:35Z RXNO MOP:0000572 alcohol oxidation MOP:0000572 An oxidation process where an alcohol is transformed into a carbonyl compound. https://orcid.org/0000-0001-5985-7429 An oxidation process where a primary alcohol is transformed into an aldehyde. batchelorc 2009-06-01T06:10:59Z RXNO MOP:0000573 primary alcohol oxidation to aldehyde MOP:0000573 An oxidation process where a primary alcohol is transformed into an aldehyde. https://orcid.org/0000-0001-5985-7429 An oxidation process where a secondary alcohol is transformed into a ketone. batchelorc 2009-06-01T06:11:31Z RXNO MOP:0000574 secondary alcohol oxidation to ketone MOP:0000574 An oxidation process where a secondary alcohol is transformed into a ketone. https://orcid.org/0000-0001-5985-7429 An oxidation process where an amine is transformed into an imine. batchelorc 2009-06-01T06:15:40Z RXNO MOP:0000575 amine oxidation MOP:0000575 An oxidation process where an amine is transformed into an imine. https://orcid.org/0000-0001-5985-7429 A reduction process where an imine is transformed into an amine. batchelorc 2009-06-01T06:19:21Z RXNO MOP:0000576 imine reduction MOP:0000576 A reduction process where an imine is transformed into an amine. https://orcid.org/0000-0001-5985-7429 A reduction process where the oxidation state carbonyl carbon in the ester functionality is reduced. batchelorc 2009-06-02T05:30:48Z reduction of ester RXNO MOP:0000577 ester reduction MOP:0000577 A reduction process where the oxidation state carbonyl carbon in the ester functionality is reduced. https://orcid.org/0000-0001-5985-7429 An ester reduction where the product is the corresponding aldehyde. batchelorc 2009-06-02T05:31:49Z reduction of ester to aldehyde reduction of esters to aldehyde RXNO MOP:0000578 ester reduction to aldehyde MOP:0000578 An ester reduction where the product is the corresponding aldehyde. https://orcid.org/0000-0001-5985-7429 An ester reduction where the product is the corresponding primary alcohol. batchelorc 2009-06-02T05:32:37Z reduction of ester to primary alcohol reduction of esters to primary alcohol RXNO MOP:0000579 ester reduction to primary alcohol MOP:0000579 An ester reduction where the product is the corresponding primary alcohol. https://orcid.org/0000-0001-5985-7429 A reduction process where a ketone is reduced to a secondary alcohol. batchelorc 2009-06-02T05:35:42Z reduction of ketone reduction of ketones RXNO MOP:0000580 ketone reduction MOP:0000580 A reduction process where a ketone is reduced to a secondary alcohol. https://orcid.org/0000-0001-5985-7429 An oxidation process where the oxidation state of at least one doubly-bonded carbon atom increases. batchelorc 2009-06-02T05:45:30Z olefin oxidation RXNO MOP:0000581 alkene oxidation MOP:0000581 An oxidation process where the oxidation state of at least one doubly-bonded carbon atom increases. https://orcid.org/0000-0001-5985-7429 An alkene oxidation where the product is the corresponding 1,2-diol. batchelorc 2009-06-02T05:46:52Z alkene oxidation to glycol oxidation of alkene to 1,2-diol oxidation of alkenes to 1,2-diol RXNO MOP:0000582 alkene oxidation to 1,2-diol MOP:0000582 An alkene oxidation where the product is the corresponding 1,2-diol. https://orcid.org/0000-0001-5985-7429 An alkene oxidation where the reagent is ozone and the product is the corresponding ozonide. batchelorc 2009-06-02T05:48:42Z ozonolysis of alkene ozonolysis of alkenes RXNO MOP:0000583 alkene ozonolysis MOP:0000583 An alkene oxidation where the reagent is ozone and the product is the corresponding ozonide. https://orcid.org/0000-0001-5985-7429 An alkene oxidation process where the reactant is a primary alkene and the products are carboxylic acid and carbon dioxide. This can be achieved with a warm, acidic solution of potassium permanganate. batchelorc 2009-06-02T06:02:46Z RXNO MOP:0000584 primary alkene oxidation to carboxylic acid and carbon dioxide MOP:0000584 An alkene oxidation process where the reactant is a primary alkene and the products are carboxylic acid and carbon dioxide. This can be achieved with a warm, acidic solution of potassium permanganate. https://orcid.org/0000-0001-5985-7429 An alkene oxidation where the reactant is a tertiary alkene and the products are the corresponding carboxylic acid and ketone. This can be achieved with a warm, acidic solution of potassium permanganate. batchelorc 2009-06-02T06:04:14Z RXNO MOP:0000585 tertiary alkene oxidation to carboxylic acid and ketone MOP:0000585 An alkene oxidation where the reactant is a tertiary alkene and the products are the corresponding carboxylic acid and ketone. This can be achieved with a warm, acidic solution of potassium permanganate. https://orcid.org/0000-0001-5985-7429 An alkene oxidation process where the reactant is a secondary alkene and the products are the corresponding aldehydes. This can be achieved with warm, acidic potassium permanganate. batchelorc 2009-06-02T06:06:23Z RXNO MOP:0000586 secondary, non-terminal alkene oxidation to aldehydes MOP:0000586 An alkene oxidation process where the reactant is a secondary alkene and the products are the corresponding aldehydes. This can be achieved with warm, acidic potassium permanganate. https://orcid.org/0000-0001-5985-7429 An alkene oxidation process where the reactant is a secondary terminal alkene and the products are carbon dioxide and the corresponding ketone. This can be achieved by warm, acidic potassium permanganate solution. batchelorc 2009-06-02T06:07:44Z RXNO MOP:0000587 secondary terminal alkene oxidation to ketone and carbon dioxide MOP:0000587 An alkene oxidation process where the reactant is a secondary terminal alkene and the products are carbon dioxide and the corresponding ketone. This can be achieved by warm, acidic potassium permanganate solution. https://orcid.org/0000-0001-5985-7429 An alkene oxidation process where the reactant is a quaternary alkene and the products are the corresponding ketones. batchelorc 2009-06-02T06:09:24Z RXNO MOP:0000588 quaternary alkene oxidation to ketones MOP:0000588 An alkene oxidation process where the reactant is a quaternary alkene and the products are the corresponding ketones. https://orcid.org/0000-0001-5985-7429 A reduction process that involves addition of hydrogen atoms across a double bond. batchelorc 2009-06-05T04:53:34Z RXNO MOP:0000589 hydrogenation MOP:0000589 A reduction process that involves addition of hydrogen atoms across a double bond. https://orcid.org/0000-0001-5985-7429 Formation of a covalent bond between a substrate and a pseudohalo group. RXNO MOP:0000596 pseudohalogenation MOP:0000596 Formation of a covalent bond between a substrate and a pseudohalo group. RSC:xp A molecular process where a molecule is broken up by reaction with a molecule that is part of the solvent material. It may be the primary constituent molecule of the solvent material (for example water, ethanol, ammonia) or its lyonium ion or lyate ion. batchelorc 2009-09-16T11:11:24Z RXNO MOP:0000618 solvolysis MOP:0000618 A molecular process where a molecule is broken up by reaction with a molecule that is part of the solvent material. It may be the primary constituent molecule of the solvent material (for example water, ethanol, ammonia) or its lyonium ion or lyate ion. AU:S05762 https://orcid.org/0000-0001-5985-7429 A solvolysis reaction where the solvent material is water. batchelorc 2009-09-16T11:13:21Z RXNO MOP:0000619 hydrolysis MOP:0000619 A solvolysis reaction where the solvent material is water. https://orcid.org/0000-0001-5985-7429 A reaction in which two or more reactants or remote reactive sites within the same molecular entity yield a single main product with accompanying formation of a small molecule. batchelorc 2009-09-16T11:30:32Z RXNO:0000315 RXNO MOP:0000627 condensation reaction MOP:0000627 A reaction in which two or more reactants or remote reactive sites within the same molecular entity yield a single main product with accompanying formation of a small molecule. AU:C01238 A condensation reaction where the small molecule produced is water. batchelorc 2009-09-16T11:32:33Z RXNO MOP:0000628 molecular dehydration reaction MOP:0000628 A condensation reaction where the small molecule produced is water. https://orcid.org/0000-0001-5985-7429 A reaction of two or more reacting molecular entities resulting in a single reaction product containing all atoms of all components with formation of two chemical bonds and a net reduction in bond multiplicity. RXNO MOP:0000642 addition reaction MOP:0000642 A reaction of two or more reacting molecular entities resulting in a single reaction product containing all atoms of all components with formation of two chemical bonds and a net reduction in bond multiplicity. https://doi.org/10.1351/goldbook.A00133 Formation of a covalent bond between a substrate and an amino group. RXNO MOP:0000650 amination MOP:0000650 Formation of a covalent bond between a substrate and an amino group. https://orcid.org/0000-0001-5985-7429 A molecular process where two groups are lost with concomitant formation of an unsaturation in the molecule or formation of a new ring. RXNO MOP:0000656 elimination reaction MOP:0000656 A molecular process where two groups are lost with concomitant formation of an unsaturation in the molecule or formation of a new ring. doi:10.1351/goldbook.E02038 A cyclisation that results in the formation of an epoxide. RXNO MOP:0000671 epoxidation MOP:0000671 A cyclisation that results in the formation of an epoxide. https://orcid.org/0000-0001-5985-7429 An oxidation process where the oxidation state of at least one sulfur atom increases. RXNO MOP:0000705 oxidation at sulfur MOP:0000705 An oxidation process where the oxidation state of at least one sulfur atom increases. https://orcid.org/0000-0001-5985-7429 An oxidation process where the oxidation state of at least one nitrogen atom increases. RXNO MOP:0000706 oxidation at nitrogen MOP:0000706 An oxidation process where the oxidation state of at least one nitrogen atom increases. https://orcid.org/0000-0001-5985-7429 A formal account of the degree of oxidation of an atom. http://goldbook.iupac.org/O04365.html RXNO MOP:0000712 It turns out to be formally defined, which makes our definitions a bit poor. oxidation state MOP:0000712 A formal account of the degree of oxidation of an atom. https://orcid.org/0000-0001-5985-7429 Formation of a covalent bond between a molecule and a carboxy group. RXNO MOP:0000713 carboxylation MOP:0000713 Formation of a covalent bond between a molecule and a carboxy group. RSC:xp Oxidation of a carbonyl group to an alkyne. RXNO MOP:0000714 carbonyl oxidation to alkyne MOP:0000714 Oxidation of a carbonyl group to an alkyne. https://orcid.org/0000-0001-5985-7429 A cycloaddition in which one participant contributes three electrons and the other participant contributes two electrons to the transformation of reactants to products. RXNO MOP:0000715 [3+2] cycloaddition MOP:0000715 A cycloaddition in which one participant contributes three electrons and the other participant contributes two electrons to the transformation of reactants to products. https://orcid.org/0000-0001-5985-7429 Molecular process in which an aldehyde or ketone tautomerises to form an enol. enolization RXNO MOP:0000716 enolisation MOP:0000716 Molecular process in which an aldehyde or ketone tautomerises to form an enol. https://orcid.org/0000-0001-5985-7429 Disposition that is realised in the process of enolisation RXNO MOP:0000717 enolisability MOP:0000717 Disposition that is realised in the process of enolisation https://orcid.org/0000-0001-5985-7429 A carbonyl compound that bears the disposition to be enolised. RXNO MOP:0000718 this surely belongs in ChEBI but put it here pro tem enolisable carbonyl compound MOP:0000718 A carbonyl compound that bears the disposition to be enolised. https://orcid.org/0000-0001-5985-7429 Breaking of a covalent bond between an alkyl group and an oxygen atom. RXNO MOP:0000719 O-dealkylation MOP:0000719 Breaking of a covalent bond between an alkyl group and an oxygen atom. RSC:xp A cycloaddition in which two participants contribute two electrons and the other participant contributes one electron to the transformation of reactants to products. RXNO MOP:0000720 [2+2+1] cycloaddition MOP:0000720 A cycloaddition in which two participants contribute two electrons and the other participant contributes one electron to the transformation of reactants to products. https://orcid.org/0000-0001-5985-7429 RXNO:0000027 RXNO MOP:0000721 This term was obsoleted from the RXNO namespace and transferred to MOP because it is a process identifiable by its mechanism rather than the intention of the experimenter. [3,3]-sigmatropic rearrangement MOP:0000721 A reaction in which two or more reactants or remote reactive sites within the same molecular entity yield a single main product with accompanying formation of a carbon dioxide molecule. batchelorc 2014-03-05T10:00:00Z RXNO MOP:0000722 decarboxylative condensation MOP:0000722 A reaction in which two or more reactants or remote reactive sites within the same molecular entity yield a single main product with accompanying formation of a carbon dioxide molecule. RSC:xp A reaction in which two or more reactants or remote reactive sites within the same molecular entity yield a single main product with accompanying formation of an ethanol molecule. batchelorc 2014-03-05T10:00:00Z RXNO MOP:0000723 deethanolative condensation MOP:0000723 A reaction in which two or more reactants or remote reactive sites within the same molecular entity yield a single main product with accompanying formation of an ethanol molecule. RSC:xp batchelorc 2014-04-09T10:00:00Z RXNO MOP:0000730 Brønsted acid catalysis MOP:0000730 batchelorc 2014-04-09T10:00:00Z RXNO MOP:0000731 base catalysis MOP:0000731 batchelorc 2014-04-09T10:00:00Z RXNO MOP:0000732 hydron donation MOP:0000732 batchelorc 2014-04-09T10:00:00Z RXNO MOP:0000733 accepting an electron pair in Lewis adduct formation MOP:0000733 batchelorc 2014-04-09T10:00:00Z RXNO MOP:0000734 Lewis acid catalysis MOP:0000734 batchelorc 2014-04-09T10:00:00Z RXNO MOP:0000735 Lewis base catalysis MOP:0000735 batchelorc 2014-04-09T10:00:00Z RXNO MOP:0000736 Brønsted base catalysis MOP:0000736 batchelorc 2014-04-09T10:00:00Z RXNO MOP:0000737 accepting a hydron MOP:0000737 batchelorc 2014-04-09T10:00:00Z RXNO MOP:0000738 electron pair donation in Lewis adduct formation MOP:0000738 RXNO MOP:0000739 Lewis adduct formation MOP:0000739 Catalysis of a reaction where the catalyst either donates a hydron or accepts an electron pair. RXNO MOP:0000740 acid catalysis MOP:0000740 Catalysis of a reaction where the catalyst either donates a hydron or accepts an electron pair. https://orcid.org/0000-0001-5985-7429 A reaction in which one singly-bonded group, but not the hydrogen atom, is replaced by another singly-bonded group. RXNO:0000019 RXNO MOP:0000790 The Gold Book says hydrogen atoms count, but this differs from everyone's intuition. See http://goldbook.iupac.org/S06078.html substitution reaction MOP:0000790 A reaction in which one singly-bonded group, but not the hydrogen atom, is replaced by another singly-bonded group. https://orcid.org/0000-0001-5985-7429 A substitution reaction in which one singly-bonded substituent on an aromatic skeleton is replaced by another singly-bonded substituent. RXNO:0000020 RXNO MOP:0000791 aromatic substitution MOP:0000791 A substitution reaction in which one singly-bonded substituent on an aromatic skeleton is replaced by another singly-bonded substituent. https://orcid.org/0000-0001-5985-7429 A substitution reaction in an allylic system with concomitant migration of the allyl double bond. RXNO:0000033 RXNO MOP:0000792 allylic rearrangement MOP:0000792 A substitution reaction in an allylic system with concomitant migration of the allyl double bond. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A substitution reaction where the reactive centre is a nitrogen atom. RXNO:0000319 RXNO MOP:0000793 N-substitution MOP:0000793 A substitution reaction where the reactive centre is a nitrogen atom. https://orcid.org/0000-0001-5985-7429 A substitution reaction where the reactive centre is an oxygen atom. RXNO:0000318 NAMERXN:1.7 RXNO MOP:0000794 O-substitution MOP:0000794 A substitution reaction where the reactive centre is an oxygen atom. https://orcid.org/0000-0001-5985-7429 A substitution reaction where the reactive centre is a sulfur atom. batchelorc 2012-03-22T12:22:59Z RXNO:0000336 NAMERXN:1.8 RXNO MOP:0000795 S-substitution MOP:0000795 A substitution reaction where the reactive centre is a sulfur atom. https://orcid.org/0000-0001-5985-7429 Formation of a covalent bond with a group where the free valence is on a nitrogen centre. RXNO MOP:0000802 formation of covalent bond with nitrogen centre MOP:0000802 Formation of a covalent bond with a group where the free valence is on a nitrogen centre. https://orcid.org/0000-0001-5985-7429 A reaction in which two or more reactants or remote reactive sites within the same molecular entity yield a single main product with accompanying formation of an alcohol molecule. RXNO MOP:0000825 dealcoholative condensation MOP:0000825 A reaction in which two or more reactants or remote reactive sites within the same molecular entity yield a single main product with accompanying formation of an alcohol molecule. https://orcid.org/0000-0001-5985-7429 A disposition which is realised in a [4+2] reaction with a double-bonded system. http://goldbook.iupac.org/D01700.html RXNO MOP:0000826 dienophilicity MOP:0000826 A disposition which is realised in a [4+2] reaction with a double-bonded system. https://orcid.org/0000-0001-5985-7429 Breaking of a covalent bond between an alkyl group and a substrate. RXNO MOP:0001369 dealkylation MOP:0001369 Breaking of a covalent bond between an alkyl group and a substrate. RSC:xp Breaking of a covalent bond between a substrate and an organyl group. RXNO MOP:0001458 has_participant: CHEBI:33249 deorganylation MOP:0001458 Breaking of a covalent bond between a substrate and an organyl group. RSC:xp Breaking of a covalent bond between a substrate and a halo group. RXNO MOP:0001550 has_participant: CHEBI:47854 dehalogenation MOP:0001550 Breaking of a covalent bond between a substrate and a halo group. RSC:xp Breaking of a covalent bond between a molecule and a carboxy group. RXNO MOP:0001713 decarboxylation MOP:0001713 Breaking of a covalent bond between a molecule and a carboxy group. RSC:xp Formation of a covalent bond between a nitrogen atom in a substrate and a methyl group. RXNO MOP:0002364 has_participant: CHEBI:32875 N-methylation MOP:0002364 Formation of a covalent bond between a nitrogen atom in a substrate and a methyl group. RSC:xp Formation of a covalent bond between a nitrogen atom in a substrate and an alkyl group. RXNO MOP:0002369 has_participant: CHEBI:22323 N-alkylation MOP:0002369 Formation of a covalent bond between a nitrogen atom in a substrate and an alkyl group. RSC:xp Formation of a covalent bond between a nitrogen atom in a substrate and an aryl group. RXNO MOP:0002411 N-arylation MOP:0002411 Formation of a covalent bond between a nitrogen atom in a substrate and an aryl group. RSC:xp Formation of a covalent bond between a nitrogen atom in a substrate and an acyl group. RXNO MOP:0002479 has_participant: CHEBI:22221 N-acylation MOP:0002479 Formation of a covalent bond between a nitrogen atom in a substrate and an acyl group. RSC:xp Formation of a covalent bond between a nitrogen atom in a substrate and a sulfonyl group. RXNO MOP:0002524 has_participant: CHEBI:29825 N-sulfonylation MOP:0002524 Formation of a covalent bond between a nitrogen atom in a substrate and a sulfonyl group. RSC:xp Formation of a covalent bond between an oxygen atom in a substrate and a silyl group. RXNO MOP:0003339 has_participant: CHEBI:30541 O-silylation MOP:0003339 Formation of a covalent bond between an oxygen atom in a substrate and a silyl group. RSC:xp Formation of a covalent bond between an oxygen atom in a substrate and an acyl group. RXNO MOP:0003479 has_participant: CHEBI:22221 O-acylation MOP:0003479 Formation of a covalent bond between an oxygen atom in a substrate and an acyl group. RSC:xp Formation of a covalent bond between an oxygen atom in a substrate and a sulfonyl group. RXNO MOP:0003524 has_participant: CHEBI:29825 O-sulfonylation MOP:0003524 Formation of a covalent bond between an oxygen atom in a substrate and a sulfonyl group. RSC:xp The formation of a covalent bond between a phosphorus atom and an alkyl group. RXNO MOP:0006369 P-alkylation MOP:0006369 The formation of a covalent bond between a phosphorus atom and an alkyl group. RSC:xp RXNO OBI:0000011 planned process OBI:0000011 A reaction where the number of atoms in the molecular skeleton increases. coupling reaction RXNO RXNO:0000000 molecular skeleton joining reaction RXNO:0000000 A reaction where the number of atoms in the molecular skeleton increases. https://orcid.org/0000-0001-5985-7429 A molecular process with which the experimenters aim to achieve a particular molecular transformation. RXNO RXNO:0000001 planned reaction step RXNO:0000001 A molecular process with which the experimenters aim to achieve a particular molecular transformation. https://orcid.org/0000-0001-5985-7429 A reaction where a bond is formed between two carbon atoms. NAMERXN:3 RXNO RXNO:0000002 carbon-carbon coupling reaction RXNO:0000002 A reaction where a bond is formed between two carbon atoms. https://orcid.org/0000-0001-5985-7429 An aldol condensation where an aryl aldehyde reacts with an acid anhydride to form a cinnamic acid. https://www.rsc.org/Merck-Index/reaction/r327/ https://www.wikidata.org/wiki/Q898605 RXNO RXNO:0000003 Perkin reaction RXNO:0000003 An aldol condensation where an aryl aldehyde reacts with an acid anhydride to form a cinnamic acid. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A reaction in which the number of atoms in any ring changes between the reactant and the products. RXNO RXNO:0000004 This term was obsoleted because it was a grouping term that wasn't much help. obsolete: ring reaction true RXNO:0000004 A reaction in which the number of atoms in any ring changes between the reactant and the products. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A planned reaction step where the product contains a ring that was not in any of the reactants. RXNO RXNO:0000005 ring formation reaction step RXNO:0000005 A planned reaction step where the product contains a ring that was not in any of the reactants. https://orcid.org/0000-0001-5985-7429 A [4+2] cycloaddition reaction where a diene reacts with a compound containing a double or triple bond (a dienophile) to form an unsaturated six-membered ring compound. NAMERXN:3.11.3 https://www.rsc.org/Merck-Index/reaction/r109/ https://www.wikidata.org/wiki/Q375669 Diels-Alder coupling Diels-Alder cycloaddition RXNO RXNO:0000006 Diels-Alder reaction RXNO:0000006 A [4+2] cycloaddition reaction where a diene reacts with a compound containing a double or triple bond (a dienophile) to form an unsaturated six-membered ring compound. https://orcid.org/0000-0002-4077-4719 A joining reaction where an alkene with an allylic hydrogen reacts with a compound containing a multiple bond (an enophile) to form a substituted alkene. https://www.rsc.org/Merck-Index/reaction/r129/ https://www.wikidata.org/wiki/Q26469 RXNO RXNO:0000007 ene reaction RXNO:0000007 A joining reaction where an alkene with an allylic hydrogen reacts with a compound containing a multiple bond (an enophile) to form a substituted alkene. https://orcid.org/0000-0001-5985-7429 A joining reaction where a nucleophile adds to the beta-carbon of an alpha,beta-unsaturated system (or an activated carbon-carbon bond). https://www.wikidata.org/wiki/Q2181524 nucleophilic conjugate addition RXNO RXNO:0000008 conjugate addition RXNO:0000008 A joining reaction where a nucleophile adds to the beta-carbon of an alpha,beta-unsaturated system (or an activated carbon-carbon bond). https://orcid.org/0000-0002-4077-4719 rsc:db A conjugate addition reaction where a carbon nucleophile adds to the beta-carbon of an alpha,beta-unsaturated system (or an activated carbon-carbon bond). https://www.rsc.org/Merck-Index/reaction/r281/ https://www.wikidata.org/wiki/Q642233 Michael reaction RXNO RXNO:0000009 Michael addition RXNO:0000009 A conjugate addition reaction where a carbon nucleophile adds to the beta-carbon of an alpha,beta-unsaturated system (or an activated carbon-carbon bond). RSC:db A reaction where the number of atoms in the skeleton, and their connectivity, remain the same. RXNO RXNO:0000010 functional modification RXNO:0000010 A reaction where the number of atoms in the skeleton, and their connectivity, remain the same. https://orcid.org/0000-0001-5985-7429 A reaction in which a functional group undergoes a change that does not affect the number of atoms in (or connectivity of) the skeleton of the molecule. NAMERXN:9 RXNO RXNO:0000011 functional group modification RXNO:0000011 A reaction in which a functional group undergoes a change that does not affect the number of atoms in (or connectivity of) the skeleton of the molecule. rsc:db A functional group modification reaction where a functional group is oxidised. RXNO RXNO:0000012 functional group oxidation RXNO:0000012 A functional group modification reaction where a functional group is oxidised. https://orcid.org/0000-0001-5985-7429 A functional group oxidation where an aromatic amine is transformed into an aromatic diazonium salt. diazotization RXNO RXNO:0000013 diazotisation RXNO:0000013 A functional group oxidation where an aromatic amine is transformed into an aromatic diazonium salt. https://orcid.org/0000-0002-4077-4719 A carbon-carbon coupling reaction where a Grignard reagent reacts with a compound containing an electrophilic carbon atom. A Grignard reagent is a magnesium-stabilised carbon nucleophile. An aldehyde leads to a secondary alcohol, a ketone leads to a tertiary alcohol, an ester leads to a ketone and a nitrile leads to a ketone. NAMERXN:3.7 https://www.rsc.org/Merck-Index/reaction/r177/ https://www.wikidata.org/wiki/Q337748 RXNO RXNO:0000014 Grignard reaction RXNO:0000014 A carbon-carbon coupling reaction where a Grignard reagent reacts with a compound containing an electrophilic carbon atom. A Grignard reagent is a magnesium-stabilised carbon nucleophile. An aldehyde leads to a secondary alcohol, a ketone leads to a tertiary alcohol, an ester leads to a ketone and a nitrile leads to a ketone. RSC:db A carbon-carbon coupling reaction where a carbonyl compound reacts with a phosphonium ylide to give an alkene. NAMERXN:3.8 https://www.rsc.org/Merck-Index/reaction/r468/ https://www.wikidata.org/wiki/Q909735 Wittig condensation Wittig olefination RXNO RXNO:0000015 Wittig reaction RXNO:0000015 A carbon-carbon coupling reaction where a carbonyl compound reacts with a phosphonium ylide to give an alkene. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A carbon-carbon coupling reaction where an enol or enolate reacts with a carbonyl compound to form a beta-hydroxy ketone. The name comes from aldehyde + alcohol. https://www.rsc.org/Merck-Index/reaction/r4/ https://www.wikidata.org/wiki/Q494392 aldol reaction RXNO RXNO:0000016 aldol addition RXNO:0000016 A carbon-carbon coupling reaction where an enol or enolate reacts with a carbonyl compound to form a beta-hydroxy ketone. The name comes from aldehyde + alcohol. https://orcid.org/0000-0001-5985-7429 An aldol addition where an enol or enolate reacts with a carbonyl compound to form an alpha,beta-unsaturated ketone. https://www.rsc.org/Merck-Index/reaction/r4/ https://www.wikidata.org/wiki/Q1027170 RXNO RXNO:0000017 aldol condensation RXNO:0000017 An aldol addition where an enol or enolate reacts with a carbonyl compound to form an alpha,beta-unsaturated ketone. https://orcid.org/0000-0002-4077-4719 A ring formation reaction where a 1,3-dipolar compound reacts with an alkene or alkyne to form a five-membered ring compound. https://www.wikidata.org/wiki/Q902907 Huisgen cycloaddition Huisgen reaction Huisgen's 1,3-dipolar cycloaddition RXNO RXNO:0000018 1,3-dipolar cycloaddition RXNO:0000018 A ring formation reaction where a 1,3-dipolar compound reacts with an alkene or alkyne to form a five-membered ring compound. RSC:db true RXNO:0000019 true RXNO:0000020 An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) halide or pseudohalide to form an aromatic halide or pseudohalide. https://www.rsc.org/Merck-Index/reaction/r386/ https://www.wikidata.org/wiki/Q898821 RXNO RXNO:0000021 Sandmeyer reaction RXNO:0000021 An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) halide or pseudohalide to form an aromatic halide or pseudohalide. RSC:db An aromatic substitution reaction where an aryl diazonium salt reacts with copper powder and hydrochloric acid or hydrobromic acid to form an aromatic chloride or bromide. RXNO Gattermann reaction RXNO:0000022 This is also sometimes known as the Gattermann reaction. Also doesn't work to make fluorides or iodides. Gattermann halogenation RXNO:0000022 An aromatic substitution reaction where an aryl diazonium salt reacts with copper powder and hydrochloric acid or hydrobromic acid to form an aromatic chloride or bromide. https://orcid.org/0000-0002-4077-4719 An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(II) halide to form an aromatic halide. RXNO RXNO:0000023 Koerner-Contardi reaction RXNO:0000023 An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(II) halide to form an aromatic halide. https://orcid.org/0000-0002-4077-4719 A carbon-carbon coupling reaction where an organohalide or triflate couples to a terminal olefin to produce an internal olefin, catalysed by palladium. It is stereospecific. NAMERXN:3.2 https://www.rsc.org/Merck-Index/reaction/r192/ https://www.wikidata.org/wiki/Q899916 Heck-Mizoroki reaction Mizoroki-Heck reaction RXNO RXNO:0000024 This usually produces the trans-olefin rather than the cis-. ALSO Merck Index gives a non-terminal example. Heck reaction RXNO:0000024 A carbon-carbon coupling reaction where an organohalide or triflate couples to a terminal olefin to produce an internal olefin, catalysed by palladium. It is stereospecific. RSC:db https://orcid.org/0000-0001-5985-7429 A reaction which preserves the number of rings and number of skeletal atoms and in which the molecule rearranges so that one or more atoms or groups of atoms move from one atom to another. RXNO RXNO:0000025 rearrangement step RXNO:0000025 A reaction which preserves the number of rings and number of skeletal atoms and in which the molecule rearranges so that one or more atoms or groups of atoms move from one atom to another. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A rearrangement where an oxime rearranges to form an amide. Often there is selective migration of one group. https://www.rsc.org/Merck-Index/reaction/r29/ https://www.wikidata.org/wiki/Q813746 RXNO RXNO:0000026 Beckmann rearrangement RXNO:0000026 A rearrangement where an oxime rearranges to form an amide. Often there is selective migration of one group. https://orcid.org/0000-0001-5985-7429 true RXNO:0000027 A [3,3]-sigmatropic rearrangement where a 1,5-hexadiene rearranges to form a 1,5-hexadiene. https://www.rsc.org/Merck-Index/reaction/r86/ https://www.wikidata.org/wiki/Q905087 RXNO RXNO:0000028 Cope rearrangement RXNO:0000028 A [3,3]-sigmatropic rearrangement where a 1,5-hexadiene rearranges to form a 1,5-hexadiene. https://orcid.org/0000-0001-5985-7429 A [3,3]-sigmatropic rearrangement of a 3-hydroxy-1,5-hexadiene rearranges to form a 5,6-unsaturated carbonyl compound. https://www.rsc.org/Merck-Index/reaction/r86/ https://www.wikidata.org/wiki/Q25326942 RXNO RXNO:0000029 oxy-Cope rearrangement RXNO:0000029 A [3,3]-sigmatropic rearrangement of a 3-hydroxy-1,5-hexadiene rearranges to form a 5,6-unsaturated carbonyl compound. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A joining reaction in which one or more atoms are added to the middle of a chain. RXNO RXNO:0000030 molecular skeleton insertion reaction RXNO:0000030 A joining reaction in which one or more atoms are added to the middle of a chain. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A reaction of a ketone to give an ester, in which an alkyl, benzyl or phenyl group migrates from one of the alpha-carbon centres to an adjacent oxygen, displacing an oxygen-based leaving group; the result is a formal insertion of an oxygen atom. The reaction also works with aldehydes, giving the corresponding carboxylic acid. The term "Baeyer-Villiger rearrangement" may occasionally be used in a mechanistic sense to refer specificially to the actual rearrangement step. RXNO:0000190 https://www.rsc.org/Merck-Index/reaction/r13/ https://www.wikidata.org/wiki/Q182033 B-V reaction Baeyer-Villiger oxidative rearrangement Baeyer-Villiger reaction RXNO Baeyer-Villiger rearrangement RXNO:0000031 Baeyer-Villiger oxidation RXNO:0000031 A reaction of a ketone to give an ester, in which an alkyl, benzyl or phenyl group migrates from one of the alpha-carbon centres to an adjacent oxygen, displacing an oxygen-based leaving group; the result is a formal insertion of an oxygen atom. The reaction also works with aldehydes, giving the corresponding carboxylic acid. The term "Baeyer-Villiger rearrangement" may occasionally be used in a mechanistic sense to refer specificially to the actual rearrangement step. https://orcid.org/0000-0002-4077-4719 rsc:db A carbon-carbon coupling reaction where ammonia or an amine reacts with a non-enolisable aldehyde, often methanal, and an enolisable carbonyl compound to form a beta-amino carbonyl compound. https://www.rsc.org/Merck-Index/reaction/r265/ https://www.wikidata.org/wiki/Q183055 RXNO RXNO:0000032 Mannich reaction RXNO:0000032 A carbon-carbon coupling reaction where ammonia or an amine reacts with a non-enolisable aldehyde, often methanal, and an enolisable carbonyl compound to form a beta-amino carbonyl compound. RSC:db true RXNO:0000033 A substitution where an alcohol is converted into something else. Typical reagents are a dialkyl azodicarboxylate and a triarylphosphine. The alcohol stereocentre is inverted. https://www.rsc.org/Merck-Index/reaction/r287/ https://www.wikidata.org/wiki/Q899062 RXNO RXNO:0000034 Mitsunobu reaction RXNO:0000034 A substitution where an alcohol is converted into something else. Typical reagents are a dialkyl azodicarboxylate and a triarylphosphine. The alcohol stereocentre is inverted. RSC:db https://orcid.org/0000-0002-4077-4719 A carbon-carbon coupling reaction where a stannane reacts with an organohalide or organotriflate. NAMERXN:3.4 https://www.rsc.org/Merck-Index/reaction/r415/ https://www.wikidata.org/wiki/Q899861 Stille reaction RXNO RXNO:0000035 Stille coupling RXNO:0000035 A carbon-carbon coupling reaction where a stannane reacts with an organohalide or organotriflate. RSC:db A carbon-carbon coupling reaction where an aldehyde or amine reacts with a alpha-halo ester and zinc to form a beta-hydroxy ester. https://www.rsc.org/Merck-Index/reaction/r361/ https://www.wikidata.org/wiki/Q898948 Reformatskii reaction RXNO RXNO:0000036 Reformatsky reaction RXNO:0000036 A carbon-carbon coupling reaction where an aldehyde or amine reacts with a alpha-halo ester and zinc to form a beta-hydroxy ester. https://orcid.org/0000-0001-5985-7429 A functional group modification reaction where a functional group is reduced. RXNO RXNO:0000037 functional group reduction RXNO:0000037 A functional group modification reaction where a functional group is reduced. https://orcid.org/0000-0001-5985-7429 A functional group reduction where an aldehyde or ketone carbonyl group is reduced to a methylene with zinc-mercury amalgam and hydrochloric acid. https://www.rsc.org/Merck-Index/reaction/r82/ https://www.wikidata.org/wiki/Q898480 RXNO RXNO:0000038 Clemmensen reduction RXNO:0000038 A functional group reduction where an aldehyde or ketone carbonyl group is reduced to a methylene with zinc-mercury amalgam and hydrochloric acid. RSC:db A joining reaction where a carbon-carbon bond is formed between like moieties. RXNO RXNO:0000039 carbon-carbon homocoupling reaction RXNO:0000039 A joining reaction where a carbon-carbon bond is formed between like moieties. https://orcid.org/0000-0001-5985-7429 A carbon-carbon homocoupling reaction of an aryl halide mediated by copper. https://www.rsc.org/Merck-Index/reaction/r441/ https://www.wikidata.org/wiki/Q904703 RXNO RXNO:0000040 Ullmann reaction RXNO:0000040 A carbon-carbon homocoupling reaction of an aryl halide mediated by copper. https://orcid.org/0000-0001-5985-7429 A reaction in which two or more groups of atoms are added to the molecule, resulting in a change of skeletal bond order. RXNO RXNO:0000041 addition reaction step RXNO:0000041 A reaction in which two or more groups of atoms are added to the molecule, resulting in a change of skeletal bond order. https://orcid.org/0000-0001-5985-7429 Addition of hydrogen atoms to aromatic rings by means of alkali metals in liquid ammonia. https://www.rsc.org/Merck-Index/reaction/r44/ https://www.wikidata.org/wiki/Q864996 RXNO RXNO:0000042 Birch reduction RXNO:0000042 Addition of hydrogen atoms to aromatic rings by means of alkali metals in liquid ammonia. https://orcid.org/0000-0001-5985-7429 A carbon-carbon coupling reaction of an ester and a carbonyl compound to form a beta-keto ester. https://www.rsc.org/Merck-Index/reaction/r79/ https://www.wikidata.org/wiki/Q898501 RXNO RXNO:0000043 Claisen condensation RXNO:0000043 A carbon-carbon coupling reaction of an ester and a carbonyl compound to form a beta-keto ester. https://orcid.org/0000-0002-4077-4719 A carbon-carbon coupling reaction of an aldehyde and a methylene compound. https://www.rsc.org/Merck-Index/reaction/r230/ https://www.wikidata.org/wiki/Q898972 RXNO RXNO:0000044 Knoevenagel condensation RXNO:0000044 A carbon-carbon coupling reaction of an aldehyde and a methylene compound. https://orcid.org/0000-0001-5985-7429 A carbon-carbon coupling reaction between an arene and a carbonyl compound (usually an acyl halide) to give an aryl ketone. The reaction is catalysed by a Lewis acid. https://www.rsc.org/Merck-Index/reaction/r158/ https://www.wikidata.org/wiki/Q15130933 RXNO RXNO:0000045 Friedel-Crafts acylation RXNO:0000045 A carbon-carbon coupling reaction between an arene and a carbonyl compound (usually an acyl halide) to give an aryl ketone. The reaction is catalysed by a Lewis acid. RSC:db https://orcid.org/0000-0002-4077-4719 A carbon-carbon coupling reaction between an arene and an alkyl halide/alkene/alcohol (anything that can form a carbocation) to give a substituted arene. The reaction is catalysed by a Lewis acid. https://www.rsc.org/Merck-Index/reaction/r158/ RXNO RXNO:0000046 It proceeds by an SN1 mechanism. Friedel-Crafts alkylation RXNO:0000046 A carbon-carbon coupling reaction between an arene and an alkyl halide/alkene/alcohol (anything that can form a carbocation) to give a substituted arene. The reaction is catalysed by a Lewis acid. RSC:db https://orcid.org/0000-0002-4077-4719 An oxidation of a secondary alcohol to a ketone involving an equilibrium between the alcohol and a reagent ketone present in excess, catalysed by a metal alkoxide. https://www.rsc.org/Merck-Index/reaction/r311/ https://www.wikidata.org/wiki/Q902263 RXNO RXNO:0000047 Oppenauer oxidation RXNO:0000047 An oxidation of a secondary alcohol to a ketone involving an equilibrium between the alcohol and a reagent ketone present in excess, catalysed by a metal alkoxide. RSC:db https://orcid.org/0000-0002-4077-4719 A carbon-carbon coupling between formaldehyde and an alkene to give a 1,3-diol or an allylic alcohol, catalysed by acid. https://www.rsc.org/Merck-Index/reaction/r352/ https://www.wikidata.org/wiki/Q267374 RXNO RXNO:0000048 See also "intramolecular Prins reaction". Prins reaction RXNO:0000048 A carbon-carbon coupling between formaldehyde and an alkene to give a 1,3-diol or an allylic alcohol, catalysed by acid. RSC:db https://orcid.org/0000-0002-4077-4719 A reaction between formaldehyde and an alkene to give a 1,3-dioxane, catalysed by acid. https://www.rsc.org/Merck-Index/reaction/r352/ RXNO RXNO:0000049 intramolecular Prins reaction RXNO:0000049 A reaction between formaldehyde and an alkene to give a 1,3-dioxane, catalysed by acid. RSC:db https://orcid.org/0000-0002-4077-4719 A rearrangement of a 1,2-diol to give a carbonyl compound, catalysed by acid. https://www.rsc.org/Merck-Index/reaction/r341/ https://www.wikidata.org/wiki/Q902209 RXNO RXNO:0000050 pinacol rearrangement RXNO:0000050 A rearrangement of a 1,2-diol to give a carbonyl compound, catalysed by acid. RSC:db https://orcid.org/0000-0002-4077-4719 A rearrangement of a diazoketone to give a ketene, with the elimination of molecular nitrogen. https://www.rsc.org/Merck-Index/reaction/r474/ https://www.wikidata.org/wiki/Q255452 RXNO RXNO:0000051 Wolff rearrangement RXNO:0000051 A rearrangement of a diazoketone to give a ketene, with the elimination of molecular nitrogen. RSC:db https://orcid.org/0000-0002-4077-4719 A reaction in which a fused ring system is present in a product that was not present in any of the reactants. RXNO RXNO:0000052 fused-ring-system formation RXNO:0000052 A reaction in which a fused ring system is present in a product that was not present in any of the reactants. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A cyclodehydration of a beta-phenethylamide to give a 3,4-dihydroisoquinoline. https://www.rsc.org/Merck-Index/reaction/r46/ https://www.wikidata.org/wiki/Q866098 Bischler-Napieralski 3,4-dihydroisoquinoline synthesis Bischler-Napieralski dihydroisoquinoline synthesis Bischler-Napieralski isoquinoline synthesis RXNO RXNO:0000053 Bischler-Napieralski reaction RXNO:0000053 A cyclodehydration of a beta-phenethylamide to give a 3,4-dihydroisoquinoline. RSC:db https://orcid.org/0000-0002-4077-4719 A rearrangement of an acyl azide to give an isocyanate by pyrolysis, with the elimination of molecular nitrogen. https://www.rsc.org/Merck-Index/reaction/r97/ https://www.wikidata.org/wiki/Q254370 Curtius degradation Curtius reaction RXNO RXNO:0000054 Curtius rearrangement RXNO:0000054 A rearrangement of an acyl azide to give an isocyanate by pyrolysis, with the elimination of molecular nitrogen. RSC:db https://orcid.org/0000-0002-4077-4719 A formylation of an activated arene with a disubstituted formamide to give an arenecarbaldehyde. https://www.rsc.org/Merck-Index/reaction/r444/ https://www.wikidata.org/wiki/Q903038 Vilsmeier-Haack formylation RXNO RXNO:0000055 Vilsmeier-Haack reaction RXNO:0000055 A formylation of an activated arene with a disubstituted formamide to give an arenecarbaldehyde. RSC:db https://orcid.org/0000-0002-4077-4719 A carbon-carbon coupling reaction between a phosphonate and a carbonyl compound to give an olefin. https://www.rsc.org/Merck-Index/reaction/r468/ https://www.wikidata.org/wiki/Q905020 Emmons reaction Horner-Emmons reaction Horner-Emmons-Wadsworth reaction Horner-Wadsworth-Emmons (HWE) olefination Horner-Wadsworth-Emmons olefination Horner-Wittig reaction Wadsworth-Emmons olefination Wadsworth-Emmons reaction Wadsworth-Emmons-Horner reaction Wittig-Horner reaction RXNO RXNO:0000056 Horner-Wadsworth-Emmons reaction RXNO:0000056 A carbon-carbon coupling reaction between a phosphonate and a carbonyl compound to give an olefin. RSC:db https://orcid.org/0000-0002-4077-4719 A joining reaction between a phosphine oxide and a carbonyl compound to give an olefin. https://www.rsc.org/Merck-Index/reaction/r468/ RXNO RXNO:0000057 Horner reaction RXNO:0000057 A joining reaction between a phosphine oxide and a carbonyl compound to give an olefin. RSC:db https://orcid.org/0000-0002-4077-4719 A reaction between an alcohol or alkene and a nitrile to give an amide, catalysed by a Bronsted acid. https://www.rsc.org/Merck-Index/reaction/r372/ https://www.wikidata.org/wiki/Q902273 RXNO RXNO:0000058 Proceeds by an SN1 mechanism. Ritter reaction RXNO:0000058 A reaction between an alcohol or alkene and a nitrile to give an amide, catalysed by a Bronsted acid. RSC:db https://orcid.org/0000-0002-4077-4719 A condensation-cyclisation of a beta-phenethylamine with an aldehyde to give a tetrahydroisoquinoline. https://www.rsc.org/Merck-Index/reaction/r338/ https://www.wikidata.org/wiki/Q899206 Pictet-Spengler isoquinoline synthesis Pictet-Spengler tetrahydroisoquinoline synthesis RXNO RXNO:0000059 Pictet-Spengler reaction RXNO:0000059 A condensation-cyclisation of a beta-phenethylamine with an aldehyde to give a tetrahydroisoquinoline. RSC:db https://orcid.org/0000-0002-4077-4719 The alkylation of a trialkyl phosphite with an alkyl halide or acyl halide to give an alkyl phosphonate. RXNO:0000112 https://www.wikidata.org/wiki/Q630801 Michaelis-Arbuzov phosphonate synthesis Michaelis-Arbuzov reaction RXNO RXNO:0000060 Arbuzov reaction RXNO:0000060 The alkylation of a trialkyl phosphite with an alkyl halide or acyl halide to give an alkyl phosphonate. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 An aldol condensation between an aldehyde or ketone and a silyl enol ether (also known as a ketene silyl acetal) to give a beta-hydroxy carbonyl compound. https://www.wikidata.org/wiki/Q1059787 Mukaiyama aldol addition Mukaiyama aldol reaction RXNO RXNO:0000061 Mukaiyama aldol condensation RXNO:0000061 An aldol condensation between an aldehyde or ketone and a silyl enol ether (also known as a ketene silyl acetal) to give a beta-hydroxy carbonyl compound. RSC:db https://orcid.org/0000-0002-4077-4719 A condensation between an aromatic amine and glycerol to give a quinoline. https://www.rsc.org/Merck-Index/reaction/r403/ https://www.wikidata.org/wiki/Q903836 Skraup quinoline synthesis RXNO RXNO:0000062 Skraup reaction RXNO:0000062 A condensation between an aromatic amine and glycerol to give a quinoline. RSC:db https://orcid.org/0000-0002-4077-4719 A homologation reaction of a carboxylic acid to give the homologated carboxylic acid via acyl chloride and diazoketone intermediates. https://www.rsc.org/Merck-Index/reaction/r10/ https://www.wikidata.org/wiki/Q137617 Arndt-Eistert synthesis RXNO RXNO:0000063 This is an insertion because the carbon atom is added between the R group and the carboxyl carbon in the starting material. Arndt-Eistert reaction RXNO:0000063 A homologation reaction of a carboxylic acid to give the homologated carboxylic acid via acyl chloride and diazoketone intermediates. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 Reaction of an aldehyde or ketone with a phenylhydrazine to give an indole. https://www.wikidata.org/wiki/Q901218 Fischer indolisation Fischer indolization RXNO RXNO:0000064 Fischer indole synthesis RXNO:0000064 Reaction of an aldehyde or ketone with a phenylhydrazine to give an indole. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 An intramolecular cyclisation of a diester to give a cyclic beta-ketoester. https://www.rsc.org/Merck-Index/reaction/r108/ https://www.wikidata.org/wiki/Q900932 Dieckmann condensation Dieckmann cyclization Dieckmann reaction RXNO RXNO:0000065 This is the intramolecular version of the Claisen condensation. Dieckmann cyclisation RXNO:0000065 An intramolecular cyclisation of a diester to give a cyclic beta-ketoester. RSC:db https://orcid.org/0000-0002-4077-4719 A joining of an organic azide and a tertiary phosphine to give a phosphazo compound. https://www.wikidata.org/wiki/Q903726 Staudinger ligation Staudinger reduction RXNO RXNO:0000066 Hydrolysis of the phosphazo compound gives the corresponding amine." [https://orcid.org/0000-0002-4077-4719, RSC:db] Staudinger reaction RXNO:0000066 A joining of an organic azide and a tertiary phosphine to give a phosphazo compound. RSC:db https://orcid.org/0000-0002-4077-4719 A rearrangement of a hydrazobenzene to give a diaminobiphenyl compound. https://www.rsc.org/Merck-Index/reaction/r33/ https://www.wikidata.org/wiki/Q465781 RXNO RXNO:0000067 benzidine rearrangement RXNO:0000067 A rearrangement of a hydrazobenzene to give a diaminobiphenyl compound. RSC:db https://orcid.org/0000-0002-4077-4719 A rearrangement of a p-substituted hydrazobenzene to give a p-aminodiphenylamine. https://www.rsc.org/Merck-Index/reaction/r33/ RXNO RXNO:0000068 semidine rearrangement RXNO:0000068 A rearrangement of a p-substituted hydrazobenzene to give a p-aminodiphenylamine. RSC:db https://orcid.org/0000-0002-4077-4719 A rearrangement of a heterocyclic compound in which endocyclic and exocyclic heteroatoms swap places. https://www.rsc.org/Merck-Index/reaction/r111/ https://www.wikidata.org/wiki/Q902659 RXNO RXNO:0000069 Dimroth rearrangement RXNO:0000069 A rearrangement of a heterocyclic compound in which endocyclic and exocyclic heteroatoms swap places. RSC:db https://orcid.org/0000-0002-4077-4719 A molecular skeleton joining reaction in which a chain part of a molecular skeleton is lengthened. RXNO RXNO:0000070 chain lengthening RXNO:0000070 A molecular skeleton joining reaction in which a chain part of a molecular skeleton is lengthened. https://orcid.org/0000-0001-5985-7429 A cleaving reaction in which a peptide is treated with phenylisothiocyanate, removing the terminal amino acid group, to form the chain-shortened amine and a phenylthiohydantoin. https://www.rsc.org/Merck-Index/reaction/r122/ https://www.wikidata.org/wiki/Q898506 RXNO RXNO:0000071 The latter can be used to identify the terminal amino acid, and the process repeated to enable peptide sequencing." Edman degradation RXNO:0000071 A cleaving reaction in which a peptide is treated with phenylisothiocyanate, removing the terminal amino acid group, to form the chain-shortened amine and a phenylthiohydantoin. RSC:db https://orcid.org/0000-0002-4077-4719 A formylation reaction between a phenol and chloroform (for example, to form an ortho-formyl phenol). https://www.rsc.org/Merck-Index/reaction/r362/ RXNO RXNO:0000072 Reimer-Tiemann reaction RXNO:0000072 A formylation reaction between a phenol and chloroform (for example, to form an ortho-formyl phenol). RSC:db https://orcid.org/0000-0002-4077-4719 A reaction where atoms are lost from the molecular skeleton. RXNO RXNO:0000073 cleaving reaction RXNO:0000073 A reaction where atoms are lost from the molecular skeleton. https://orcid.org/0000-0001-5985-7429 A carbon-carbon homocoupling reaction of two molecules of an alkyl halide with sodium to give a symmetrical product. https://www.rsc.org/Merck-Index/reaction/r478/ https://www.wikidata.org/wiki/Q898901 Wurtz coupling RXNO RXNO:0000074 Wurtz reaction RXNO:0000074 A carbon-carbon homocoupling reaction of two molecules of an alkyl halide with sodium to give a symmetrical product. RSC:db https://orcid.org/0000-0002-4077-4719 A rearrangement of a 1,2-diketone to an alpha-hydroxy carboxylic acid. It can also be applied to alpha-keto aldehydes. The first exmaple of this reaction was with benzil (PhC(=O)C(=O)Ph) to form benzilic acid, hence the name. https://www.rsc.org/Merck-Index/reaction/r34/ https://www.wikidata.org/wiki/Q818488 RXNO RXNO:0000075 benzilic acid rearrangement RXNO:0000075 A rearrangement of a 1,2-diketone to an alpha-hydroxy carboxylic acid. It can also be applied to alpha-keto aldehydes. The first exmaple of this reaction was with benzil (PhC(=O)C(=O)Ph) to form benzilic acid, hence the name. RSC:db https://orcid.org/0000-0002-4077-4719 A carbon-carbon coupling of an aldehyde to an activated alkene in the presence of a nucleophilic base to give an alpha-hydroxyalkylated compound. https://www.rsc.org/Merck-Index/reaction/r27/ https://www.wikidata.org/wiki/Q812563 MBH reaction Morita-Baylis-Hillman reaction RXNO RXNO:0000076 Baylis-Hillman reaction RXNO:0000076 A carbon-carbon coupling of an aldehyde to an activated alkene in the presence of a nucleophilic base to give an alpha-hydroxyalkylated compound. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A coupling of an aldehyde or ketone with an alpha-halo ester to form an alpha,beta-epoxy ester, which hydrolyses to yield aldehydes or ketones by elimination of carbon dioxide. https://www.rsc.org/Merck-Index/reaction/r101/ https://www.wikidata.org/wiki/Q899351 Darzens condensation Darzens-Claisen reaction glycidic ester condensation RXNO RXNO:0000077 Darzens reaction RXNO:0000077 A coupling of an aldehyde or ketone with an alpha-halo ester to form an alpha,beta-epoxy ester, which hydrolyses to yield aldehydes or ketones by elimination of carbon dioxide. RSC:db https://orcid.org/0000-0002-4077-4719 A reaction in which a functional group is modified by converting it into a protecting group, in order to make subsequent reactions more selective. NAMERXN:5 RXNO RXNO:0000078 protection reaction RXNO:0000078 A reaction in which a functional group is modified by converting it into a protecting group, in order to make subsequent reactions more selective. https://orcid.org/0000-0001-5985-7429 A protection reaction in which an amine is converted into a tert-butoxycarbonyl compound. RXNO RXNO:0000079 Boc protection RXNO:0000079 A protection reaction in which an amine is converted into a tert-butoxycarbonyl compound. RSC:db https://orcid.org/0000-0002-4077-4719 A carbon-carbon coupling reaction in which an alpha-silyl carbanion reacts with an aldehyde or a ketone to give an alkene, proceeding via a beta-hydroxysilane. The stereochemistry of the alkene can be controlled by treating the intermediate with acid or base. https://www.rsc.org/Merck-Index/reaction/r331/ https://www.wikidata.org/wiki/Q900350 Peterson reaction RXNO RXNO:0000080 Peterson olefination RXNO:0000080 A carbon-carbon coupling reaction in which an alpha-silyl carbanion reacts with an aldehyde or a ketone to give an alkene, proceeding via a beta-hydroxysilane. The stereochemistry of the alkene can be controlled by treating the intermediate with acid or base. RSC:db https://orcid.org/0000-0002-4077-4719 A coupling reaction in which a phenol is coupled to an aryl halide to give a diaryl ether in the presence of a copper compound. https://www.wikidata.org/wiki/Q2371705 Ullmann ether synthesis RXNO RXNO:0000081 Ullmann condensation RXNO:0000081 A coupling reaction in which a phenol is coupled to an aryl halide to give a diaryl ether in the presence of a copper compound. RSC:db https://orcid.org/0000-0002-4077-4719 A coupling reaction in which an acetanilide is coupled to an aryl halide to give an N-acetyl diaryl amine in the presence of a copper compound. RXNO RXNO:0000082 Goldberg reaction RXNO:0000082 A coupling reaction in which an acetanilide is coupled to an aryl halide to give an N-acetyl diaryl amine in the presence of a copper compound. RSC:db https://orcid.org/0000-0002-4077-4719 A photochemical cycloaddition between an aldehyde or ketone and an alkene to give an oxetane. https://www.rsc.org/Merck-Index/reaction/r319/ https://www.wikidata.org/wiki/Q902254 Paterno-Buchi reaction RXNO RXNO:0000083 Paternò–Büchi reaction RXNO:0000083 A photochemical cycloaddition between an aldehyde or ketone and an alkene to give an oxetane. RSC:db https://orcid.org/0000-0002-4077-4719 A joining reaction between an aldehyde or ketone and an alkyl halide or aryl halide or vinyl halide or allyl halide in the presence of metal to give a secondary or tertiary alcohol. https://www.wikidata.org/wiki/Q807848 RXNO RXNO:0000084 Barbier reaction RXNO:0000084 A joining reaction between an aldehyde or ketone and an alkyl halide or aryl halide or vinyl halide or allyl halide in the presence of metal to give a secondary or tertiary alcohol. RSC:db https://orcid.org/0000-0002-4077-4719 A reductive coupling reaction between two esters to give an acyloin (an alpha-hydroxyketone). https://www.rsc.org/Merck-Index/reaction/r2/ https://www.wikidata.org/wiki/Q345007 RXNO RXNO:0000085 acyloin condensation RXNO:0000085 A reductive coupling reaction between two esters to give an acyloin (an alpha-hydroxyketone). RSC:db https://orcid.org/0000-0002-4077-4719 A carbon-carbon coupling reaction between a nitroalkane and an aldehyde or ketone to give a beta-hydroxy nitroalkane. https://www.rsc.org/Merck-Index/reaction/r196/ https://www.wikidata.org/wiki/Q903747 nitro-aldol reaction nitroaldol reaction RXNO RXNO:0000086 Henry reaction RXNO:0000086 A carbon-carbon coupling reaction between a nitroalkane and an aldehyde or ketone to give a beta-hydroxy nitroalkane. RSC:db https://orcid.org/0000-0002-4077-4719 The photolytic oxidation of a nitrate ester to give a gamma-nitroalcohol. https://www.rsc.org/Merck-Index/reaction/r24/ https://www.wikidata.org/wiki/Q809549 RXNO RXNO:0000087 Barton reaction RXNO:0000087 The photolytic oxidation of a nitrate ester to give a gamma-nitroalcohol. RSC:db https://orcid.org/0000-0002-4077-4719 A carbon-carbon coupling reaction between an organohalide or organotriflate and an organozinc compound. The reaction is catalysed by palladium or nickel. https://www.rsc.org/Merck-Index/reaction/r299/ https://www.wikidata.org/wiki/Q902756 Negishi cross-coupling RXNO RXNO:0000088 Negishi coupling RXNO:0000088 A carbon-carbon coupling reaction between an organohalide or organotriflate and an organozinc compound. The reaction is catalysed by palladium or nickel. RSC:db https://orcid.org/0000-0002-4077-4719 A reduction of an aldehyde or ketone to an alcohol involving an equilibrium between the aldehyde or ketone and a reagent alcohol present in excess, catalysed by a metal alkoxide. This reaction is the reverse of the Oppenauer oxidation (RXNO:0000047). https://www.rsc.org/Merck-Index/reaction/r272/ https://www.wikidata.org/wiki/Q903026 RXNO RXNO:0000089 Meerwein-Ponndorf-Verley reduction RXNO:0000089 A reduction of an aldehyde or ketone to an alcohol involving an equilibrium between the aldehyde or ketone and a reagent alcohol present in excess, catalysed by a metal alkoxide. This reaction is the reverse of the Oppenauer oxidation (RXNO:0000047). RSC:db https://orcid.org/0000-0002-4077-4719 The reaction between an alkyl halide or alkyl sulfate and a metal alkoxide to give an ether. https://www.wikidata.org/wiki/Q898790 Williamson etherification RXNO RXNO:0000090 Williamson ether synthesis RXNO:0000090 The reaction between an alkyl halide or alkyl sulfate and a metal alkoxide to give an ether. RSC:db https://orcid.org/0000-0002-4077-4719 A carbon-carbon coupling reaction where a carbonyl compound reacts with a phosphonium ylide to give a terminal alkene. RXNO RXNO:0000091 Wittig methylenation RXNO:0000091 A carbon-carbon coupling reaction where a carbonyl compound reacts with a phosphonium ylide to give a terminal alkene. https://orcid.org/0000-0001-5985-7429 A Diels-Alder reaction between a diene and an imine or an azadiene and an alkene to give a six-membered nitrogen-containing ring compound. https://www.wikidata.org/wiki/Q2042393 aza Diels-Alder cycloaddition aza Diels-Alder reaction aza-Diels-Alder cycloaddition azo Diels-Alder cycloaddition azo Diels-Alder reaction azo-Diels-Alder cycloaddition azo-Diels-Alder reaction RXNO RXNO:0000092 aza-Diels-Alder reaction RXNO:0000092 A Diels-Alder reaction between a diene and an imine or an azadiene and an alkene to give a six-membered nitrogen-containing ring compound. RSC:db https://orcid.org/0000-0002-4077-4719 A cleaving reaction in which a skeletal atom or group of atoms is removed from the middle of a molecule. https://www.wikidata.org/wiki/Q31287730 RXNO RXNO:0000093 extrusion reaction RXNO:0000093 A cleaving reaction in which a skeletal atom or group of atoms is removed from the middle of a molecule. https://orcid.org/0000-0001-5985-7429 The reaction of an alpha-halosulfone to give an alkene, with the extrusion of sulfur dioxide. https://www.wikidata.org/wiki/Q1935557 Ramberg-Backlund reaction RXNO RXNO:0000094 Ramberg-Bäcklund reaction RXNO:0000094 The reaction of an alpha-halosulfone to give an alkene, with the extrusion of sulfur dioxide. RSC:db https://orcid.org/0000-0002-4077-4719 The rearrangement of an aromatic nitrosamine to a para-nitrosoaniline. https://www.wikidata.org/wiki/Q1968891 RXNO RXNO:0000095 Fischer-Hepp rearrangement RXNO:0000095 The rearrangement of an aromatic nitrosamine to a para-nitrosoaniline. RSC:db https://orcid.org/0000-0002-4077-4719 A coupling reaction of a diazonium salt with a phenol or aniline to give an azo compound. https://www.wikidata.org/wiki/Q668665 RXNO RXNO:0000096 azo coupling RXNO:0000096 A coupling reaction of a diazonium salt with a phenol or aniline to give an azo compound. RSC:db https://orcid.org/0000-0002-4077-4719 A carbon-carbon coupling reaction where an imine reacts with a alpha-halo ester and zinc to form a beta-amino ester. imino Reformatsky reaction RXNO RXNO:0000097 imino-Reformatsky reaction RXNO:0000097 A carbon-carbon coupling reaction where an imine reacts with a alpha-halo ester and zinc to form a beta-amino ester. https://orcid.org/0000-0001-5985-7429 A coupling reaction between two molecules of a terminal alkyne catalysed by Cu(I) salts. https://www.rsc.org/Merck-Index/reaction/r169/ https://www.wikidata.org/wiki/Q514335 RXNO RXNO:0000098 Glaser coupling RXNO:0000098 A coupling reaction between two molecules of a terminal alkyne catalysed by Cu(I) salts. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A coupling reaction between two molecules of a terminal alkyne using stoichiometric Cu(II) salts. https://www.rsc.org/Merck-Index/reaction/r169/ Eglinton coupling RXNO RXNO:0000099 Eglinton reaction RXNO:0000099 A coupling reaction between two molecules of a terminal alkyne using stoichiometric Cu(II) salts. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A coupling reaction between a terminal alkyne and an alkynyl halide catalysed by Cu(I) salts. https://www.rsc.org/Merck-Index/reaction/r169/ https://www.wikidata.org/wiki/Q903015 RXNO RXNO:0000100 Cadiot-Chodkiewicz coupling RXNO:0000100 A coupling reaction between a terminal alkyne and an alkynyl halide catalysed by Cu(I) salts. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The reductive amination of ketones or aldehydes with an ammonium formate or formamide to form an amine. https://www.wikidata.org/wiki/Q726513 RXNO RXNO:0000101 Leuckart reaction RXNO:0000101 The reductive amination of ketones or aldehydes with an ammonium formate or formamide to form an amine. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The reductive amination of ketones or aldehydes with an amine and formic acid to form amines. https://www.wikidata.org/wiki/Q726513 Wallach reaction RXNO RXNO:0000102 Leuckart-Wallach reaction RXNO:0000102 The reductive amination of ketones or aldehydes with an amine and formic acid to form amines. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The reaction of primary alkyl halides with sodium or potassium phthalimide, followed by hydrolysis, to give the corresponding primary amine. https://www.wikidata.org/wiki/Q123422 RXNO RXNO:0000103 Gabriel synthesis RXNO:0000103 The reaction of primary alkyl halides with sodium or potassium phthalimide, followed by hydrolysis, to give the corresponding primary amine. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The reaction of primary alkyl halides with sodium or potassium phthalimide, followed by treatment with hydrazine, to give the corresponding primary amine. RXNO RXNO:0000104 Ing-Manske procedure RXNO:0000104 The reaction of primary alkyl halides with sodium or potassium phthalimide, followed by treatment with hydrazine, to give the corresponding primary amine. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A reaction in which a single skeletal atom is removed from the end of a chain. RXNO RXNO:0000105 end-of-chain chain shortening RXNO:0000105 A reaction in which a single skeletal atom is removed from the end of a chain. https://orcid.org/0000-0001-5985-7429 The decarboxylation of silver carboxylates with halogens to give organic halides. https://www.rsc.org/Merck-Index/reaction/r215/ https://www.wikidata.org/wiki/Q902216 Borodin reaction Borodine reaction RXNO RXNO:0000106 Hunsdiecker reaction RXNO:0000106 The decarboxylation of silver carboxylates with halogens to give organic halides. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A carbon-carbon coupling reaction between a dialkyl malonate and an alkyl halide, to give a substituted acetic acid. The base/R'X treatment can be repeated to give a disubstituted product. https://www.rsc.org/Merck-Index/reaction/r264/ https://www.wikidata.org/wiki/Q902284 RXNO RXNO:0000107 malonic ester synthesis RXNO:0000107 A carbon-carbon coupling reaction between a dialkyl malonate and an alkyl halide, to give a substituted acetic acid. The base/R'X treatment can be repeated to give a disubstituted product. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A reaction in which an existing ring is increased in size. ring enlargement RXNO RXNO:0000108 ring expansion RXNO:0000108 A reaction in which an existing ring is increased in size. https://orcid.org/0000-0001-5985-7429 The reaction between isatin and an alpha-methylene carbonyl compound to give a substituted quinoline-4-carboxylic acid. https://www.rsc.org/Merck-Index/reaction/r334/ https://www.wikidata.org/wiki/Q1580484 Pfitzinger quinoline synthesis Pfitzinger-Borsche reaction RXNO RXNO:0000109 Pfitzinger reaction RXNO:0000109 The reaction between isatin and an alpha-methylene carbonyl compound to give a substituted quinoline-4-carboxylic acid. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A reaction in which the parent molecule breaks up into three or more products. RXNO RXNO:0000110 fragmentation reaction RXNO:0000110 A reaction in which the parent molecule breaks up into three or more products. https://orcid.org/0000-0001-5985-7429 The fragmentation of a molecule that takes place when an electron-donating fragment (X) and an electron-accepting fragment (X') are situated at positions 1 and 3 on an aliphatic chain, to give a cationic fragment, a neutral fragment (e.g. an alkene) and an anionic fragment. https://www.wikidata.org/wiki/Q5609896 RXNO RXNO:0000111 Grob fragmentation RXNO:0000111 The fragmentation of a molecule that takes place when an electron-donating fragment (X) and an electron-accepting fragment (X') are situated at positions 1 and 3 on an aliphatic chain, to give a cationic fragment, a neutral fragment (e.g. an alkene) and an anionic fragment. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 true RXNO:0000112 The rearrangement of an alpha-, beta- or gamma-hydroxy silane to give a silyl ether. It is catalysed by a base. https://www.rsc.org/Merck-Index/reaction/r62/ https://www.wikidata.org/wiki/Q2558021 RXNO RXNO:0000113 Brook rearrangement RXNO:0000113 The rearrangement of an alpha-, beta- or gamma-hydroxy silane to give a silyl ether. It is catalysed by a base. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The reaction of a propargylic cation (stabilised with dicobalt octacarbonyl) with a nucleophile to give a substituted alkyne. https://www.rsc.org/Merck-Index/reaction/r303/ https://www.wikidata.org/wiki/Q902932 RXNO RXNO:0000114 Nicholas reaction RXNO:0000114 The reaction of a propargylic cation (stabilised with dicobalt octacarbonyl) with a nucleophile to give a substituted alkyne. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The reaction of a propargylic cation (stabilised with dicobalt octacarbonyl) with a hydride or amine or enamine to give a substituted alkyne. RXNO RXNO:0000115 Nicholas reaction, nucleophilic heteroatom centre RXNO:0000115 The reaction of a propargylic cation (stabilised with dicobalt octacarbonyl) with a hydride or amine or enamine to give a substituted alkyne. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The reaction of a propargylic cation (stabilised with dicobalt octacarbonyl) with a nucleophilic carbon centre (on e.g. enolates, allyl silanes, ketones, electron-rich aromatics, beta-dicarbonyl compounds) to give a substituted alkyne. RXNO RXNO:0000116 Nicholas reaction, nucleophilic carbon centre RXNO:0000116 The reaction of a propargylic cation (stabilised with dicobalt octacarbonyl) with a nucleophilic carbon centre (on e.g. enolates, allyl silanes, ketones, electron-rich aromatics, beta-dicarbonyl compounds) to give a substituted alkyne. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A carbon-carbon coupling reaction between a phenyl sulfone and an aldehyde or ketone to give a (typically trans) alkene. https://www.rsc.org/Merck-Index/reaction/r224/ https://www.wikidata.org/wiki/Q902237 Julia-Lythgoe olefination RXNO RXNO:0000117 Julia olefination RXNO:0000117 A carbon-carbon coupling reaction between a phenyl sulfone and an aldehyde or ketone to give a (typically trans) alkene. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The oxidation of a benzylic halide to give an aldehyde. The reaction uses hexamethylenetetramine. https://www.wikidata.org/wiki/Q909040 RXNO RXNO:0000118 Sommelet reaction RXNO:0000118 The oxidation of a benzylic halide to give an aldehyde. The reaction uses hexamethylenetetramine. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The reduction of an ester using sodium to give two alcohols. https://www.rsc.org/Merck-Index/reaction/r58/ https://www.wikidata.org/wiki/Q895315 Bouveault-Blanc procedure Bouveault-Blanc reduction RXNO RXNO:0000119 Bouveault-Blanc reaction RXNO:0000119 The reduction of an ester using sodium to give two alcohols. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A base-catalysed isomerisation of a 2,3-epoxyalcohol, with inversion of configuration at C2. https://www.rsc.org/Merck-Index/reaction/r321/ https://www.wikidata.org/wiki/Q983127 RXNO RXNO:0000120 Payne rearrangement RXNO:0000120 A base-catalysed isomerisation of a 2,3-epoxyalcohol, with inversion of configuration at C2. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A base-catalysed isomerisation of a 2,3-epoxyamine to form a hydroxy aziridine, with inversion of configuration at C2. https://www.rsc.org/Merck-Index/reaction/r321/ RXNO RXNO:0000121 aza-Payne rearrangement RXNO:0000121 A base-catalysed isomerisation of a 2,3-epoxyamine to form a hydroxy aziridine, with inversion of configuration at C2. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The base-catalysed rearrangement of an o-acetoxyacetophenone to give a hydroxyphenyl-1,3-diketone. https://www.rsc.org/Merck-Index/reaction/r14/ https://www.wikidata.org/wiki/Q804325 RXNO RXNO:0000122 Baker-Venkataraman rearrangement RXNO:0000122 The base-catalysed rearrangement of an o-acetoxyacetophenone to give a hydroxyphenyl-1,3-diketone. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A reaction in which two or more groups of atoms are removed from the molecule, resulting in a change of skeletal bond order. RXNO RXNO:0000123 This is narrower in focus than elimination in general in that we're focussing on the aims of the chemist. molecular skeleton elimination reaction RXNO:0000123 A reaction in which two or more groups of atoms are removed from the molecule, resulting in a change of skeletal bond order. https://orcid.org/0000-0001-5985-7429 The reaction of a tosylhydrazone of an aldehyde or ketone with a strong base to give an olefin. https://www.rsc.org/Merck-Index/reaction/r16/ https://www.wikidata.org/wiki/Q575939 RXNO RXNO:0000124 This generally provides the more-substituted olefin as the thermodynamic product. Bamford-Stevens reaction RXNO:0000124 The reaction of a tosylhydrazone of an aldehyde or ketone with a strong base to give an olefin. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The reaction of a tosylhydrazone of an aldehyde or ketone with an alkyllithium or Grignard reagent to give an olefin. https://www.rsc.org/Merck-Index/reaction/r16/ https://www.wikidata.org/wiki/Q846597 RXNO RXNO:0000125 This generally provides the less-substituted olefin as the kinetic product. Shapiro reaction RXNO:0000125 The reaction of a tosylhydrazone of an aldehyde or ketone with an alkyllithium or Grignard reagent to give an olefin. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The reaction between an aromatic amine, an aldehyde and pyruvic acid on heating to give a quinoline 4-carboxylic acid (cinchoninic acid). https://www.rsc.org/Merck-Index/reaction/r114/ https://www.wikidata.org/wiki/Q3772250 RXNO RXNO:0000126 Doebner reaction RXNO:0000126 The reaction between an aromatic amine, an aldehyde and pyruvic acid on heating to give a quinoline 4-carboxylic acid (cinchoninic acid). RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The conversion of an aromatic amine to the corresponding fluoride via the diazonium fluoroborate. https://www.rsc.org/Merck-Index/reaction/r388/ https://www.wikidata.org/wiki/Q572113 Schiemann reaction RXNO RXNO:0000127 Balz-Schiemann reaction RXNO:0000127 The conversion of an aromatic amine to the corresponding fluoride via the diazonium fluoroborate. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The decarboxylation and coupling of a carboxylate or mixture of carboxylates to give a dimer. https://www.rsc.org/Merck-Index/reaction/r238/ https://www.wikidata.org/wiki/Q901771 Crum-Brown-Walker reaction Kolbe electrolytic synthesis Kolbe electrosynthesis Kolbe reaction RXNO RXNO:0000128 Kolbe electrolysis RXNO:0000128 The decarboxylation and coupling of a carboxylate or mixture of carboxylates to give a dimer. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 Reaction of a ketone or aldehyde, amine, an isocyanide and carboxylic acid to form a bisamide. https://www.rsc.org/Merck-Index/reaction/r440/ https://www.wikidata.org/wiki/Q2002373 4CC Ugi four-component condensation Ugi-4CR RXNO RXNO:0000129 Ugi reaction RXNO:0000129 Reaction of a ketone or aldehyde, amine, an isocyanide and carboxylic acid to form a bisamide. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The oxidation of a terminal alkene or ethene to a methyl ketone or acetaldehyde, catalysed by PdCl2 and CuCl2, and using molecular oxygen as the oxidant. https://www.rsc.org/Merck-Index/reaction/r452/ Wacker oxidation Wacker reaction RXNO RXNO:0000130 Wacker-Tsuji oxidation RXNO:0000130 The oxidation of a terminal alkene or ethene to a methyl ketone or acetaldehyde, catalysed by PdCl2 and CuCl2, and using molecular oxygen as the oxidant. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The oxidation of ethene to acetaldehyde, catalysed by PdCl2 and CuCl2, and using molecular oxygen as the oxidant. https://www.wikidata.org/wiki/Q578923 RXNO RXNO:0000131 Wacker process RXNO:0000131 The oxidation of ethene to acetaldehyde, catalysed by PdCl2 and CuCl2, and using molecular oxygen as the oxidant. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The reaction of carbon monoxide with methanol to form acetic acid, catalysed by a rhodium complex. https://www.wikidata.org/wiki/Q901246 RXNO RXNO:0000132 Monsanto process RXNO:0000132 The reaction of carbon monoxide with methanol to form acetic acid, catalysed by a rhodium complex. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The reaction of carbon monoxide with methanol to form acetic acid, catalysed by an iridium complex. https://www.wikidata.org/wiki/Q579304 RXNO RXNO:0000133 Cativa process RXNO:0000133 The reaction of carbon monoxide with methanol to form acetic acid, catalysed by an iridium complex. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The deoxygenation of an alcohol to the corresponding alkane using a thiochloroformate. It proceeds by a radical mechanism. https://www.rsc.org/Merck-Index/reaction/r22/ https://www.wikidata.org/wiki/Q809548 Barton deoxygenation Barton reduction RXNO RXNO:0000134 Barton-McCombie deoxygenation RXNO:0000134 The deoxygenation of an alcohol to the corresponding alkane using a thiochloroformate. It proceeds by a radical mechanism. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The decarboxylation of a carboxylic acid to the lower homologue alkane using a pyridine thione. https://www.rsc.org/Merck-Index/reaction/r21/ https://www.wikidata.org/wiki/Q3454335 RXNO RXNO:0000135 The reaction proceeds by a radical mechanism. Barton decarboxylation RXNO:0000135 The decarboxylation of a carboxylic acid to the lower homologue alkane using a pyridine thione. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The hydrogenolysis of an acyl halide to the corresponding aldehyde, catalysed by palladium-on-barium sulfate. https://www.rsc.org/Merck-Index/reaction/r375/ https://www.wikidata.org/wiki/Q905524 Rosenmund reaction RXNO RXNO:0000136 Rosenmund reduction RXNO:0000136 The hydrogenolysis of an acyl halide to the corresponding aldehyde, catalysed by palladium-on-barium sulfate. https://orcid.org/0000-0002-4077-4719 rsc:db A carbon-carbon coupling reaction where a terminal alkyne reacts with an aryl halide to give an aryl alkyne. It is catalysed by palladium. NAMERXN:3.3 https://www.rsc.org/Merck-Index/reaction/r408/ https://www.wikidata.org/wiki/Q900334 Hagihara-Sonogashira coupling Sonogashira cross-coupling Sonogashira reaction RXNO RXNO:0000137 Sonogashira coupling RXNO:0000137 A carbon-carbon coupling reaction where a terminal alkyne reacts with an aryl halide to give an aryl alkyne. It is catalysed by palladium. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A reaction between two aromatic aldehydes to give a benzoin (an alpha-hydroxyketone). https://www.rsc.org/Merck-Index/reaction/r35/ https://www.wikidata.org/wiki/Q818514 benzoin addition RXNO RXNO:0000138 benzoin condensation RXNO:0000138 A reaction between two aromatic aldehydes to give a benzoin (an alpha-hydroxyketone). RSC:db https://orcid.org/0000-0002-4077-4719 The formylation of an arene with hydrogen cyanide to give an aryl aldehyde or ketone. RXNO RXNO:0000139 This is essentially a variant of the Friedel-Crafts acylation. Gattermann reaction RXNO:0000139 The formylation of an arene with hydrogen cyanide to give an aryl aldehyde or ketone. RSC:db https://orcid.org/0000-0002-4077-4719 The coupling of a boronic acid or boronic ester with an unsaturated halide, triflate or sulfonate catalysed by a palladium(0) complex. NAMERXN:3.1 https://www.rsc.org/Merck-Index/reaction/r424/ https://www.wikidata.org/wiki/Q899891 Suzuki coupling reaction Suzuki cross-coupling Suzuki cross-coupling reaction Suzuki reaction Suzuki-Miyaura coupling Suzuki-Miyaura coupling reaction Suzuki-Miyaura cross-coupling Suzuki-Miyaura cross-coupling reaction Suzuki-Miyaura reaction RXNO RXNO:0000140 Suzuki-Miyaura coupling RXNO:0000140 The coupling of a boronic acid or boronic ester with an unsaturated halide, triflate or sulfonate catalysed by a palladium(0) complex. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The epoxidation of an allylic alcohol to give a beta,gamma-epoxy alcohol, with control of absolute stereochemistry at the two new stereocentres. The oxidising agent is tert-butyl hydroperoxide, and the catalyst is a complex of titanium salt and optically active diethyl tartrate. https://www.rsc.org/Merck-Index/reaction/r397/ https://www.wikidata.org/wiki/Q56672072 Katsuki-Sharpless asymmetric epoxidation Katsuki-Sharpless epoxidation Sharpless epoxidation Sharpless-Katsuki asymmetric epoxidation Sharpless-Katsuki epoxidation RXNO RXNO:0000141 Sharpless asymmetric epoxidation RXNO:0000141 The epoxidation of an allylic alcohol to give a beta,gamma-epoxy alcohol, with control of absolute stereochemistry at the two new stereocentres. The oxidising agent is tert-butyl hydroperoxide, and the catalyst is a complex of titanium salt and optically active diethyl tartrate. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The dihydroxylation of an alkene to give an alpha,beta-diol, with control of absolute stereochemistry at the two new stereocentres. The oxidising agent is osmium tetroxide, which is used catalytically with a stoichiometric oxidant and a chiral ligand. The reagents are available commercially as AD-mix. https://www.rsc.org/Merck-Index/reaction/r396/ https://www.wikidata.org/wiki/Q752651 Sharpless bishydroxylation Sharpless hydroxylation RXNO RXNO:0000142 Sharpless asymmetric dihydroxylation RXNO:0000142 The dihydroxylation of an alkene to give an alpha,beta-diol, with control of absolute stereochemistry at the two new stereocentres. The oxidising agent is osmium tetroxide, which is used catalytically with a stoichiometric oxidant and a chiral ligand. The reagents are available commercially as AD-mix. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The aminohydroxylation of an alkene to give a beta-amino alcohol, with control of absolute stereochemistry at the two new stereocentres. The oxidising agent is an oxygen-containing osmium species and/or an amino derivative which can be used catalytically with a stoichiometric oxidant and a chiral ligand. Sharpless oxyamination RXNO RXNO:0000143 Sharpless asymmetric aminohydroxylation RXNO:0000143 The aminohydroxylation of an alkene to give a beta-amino alcohol, with control of absolute stereochemistry at the two new stereocentres. The oxidising agent is an oxygen-containing osmium species and/or an amino derivative which can be used catalytically with a stoichiometric oxidant and a chiral ligand. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A cross-coupling reaction between a Grignard reagent and an activated (aryl or vinyl) halide or triflate. The reaction is catalysed by a palladium or nickel catalyst. https://www.rsc.org/Merck-Index/reaction/r248/ https://www.wikidata.org/wiki/Q899278 Kharasch cross-coupling Kumada cross-coupling RXNO RXNO:0000144 Kumada coupling RXNO:0000144 A cross-coupling reaction between a Grignard reagent and an activated (aryl or vinyl) halide or triflate. The reaction is catalysed by a palladium or nickel catalyst. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The degradation of a carboxylic acid to its next lower homologous carboxylic acid. https://www.rsc.org/Merck-Index/reaction/r18/ https://www.wikidata.org/wiki/Q5801440 Barbier-Wieland procedure RXNO RXNO:0000145 Barbier-Wieland degradation RXNO:0000145 The degradation of a carboxylic acid to its next lower homologous carboxylic acid. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A homologation reaction of an aldehyde to yield a terminal alkyne. The reagents are tetrabromomethane, triphenylphosphine, butyllithium and water. https://www.rsc.org/Merck-Index/reaction/r89/ https://www.wikidata.org/wiki/Q903573 Ramirez-Corey-Fuchs reaction RXNO RXNO:0000146 Corey-Fuchs reaction RXNO:0000146 A homologation reaction of an aldehyde to yield a terminal alkyne. The reagents are tetrabromomethane, triphenylphosphine, butyllithium and water. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A reduction of a quaternary ammonium salt containing at least one unsaturated substituent, to give a tertiary amine. https://www.rsc.org/Merck-Index/reaction/r127/ https://www.wikidata.org/wiki/Q2026108 Emde reaction Emde reduction RXNO RXNO:0000147 Emde degradation RXNO:0000147 A reduction of a quaternary ammonium salt containing at least one unsaturated substituent, to give a tertiary amine. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The [3,3]-sigmatropic rearrangement of an allyl vinyl ether to give a gamma,delta-unsaturated carbonyl compound. https://www.rsc.org/Merck-Index/reaction/r80/ https://www.wikidata.org/wiki/Q900936 RXNO RXNO:0000148 Claisen rearrangement RXNO:0000148 The [3,3]-sigmatropic rearrangement of an allyl vinyl ether to give a gamma,delta-unsaturated carbonyl compound. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The enolisation and subsequent [3,3]-sigmatropic rearrangement of an allylic acetate to give a gamma,delta-unsaturated carboxylic acid. https://www.rsc.org/Merck-Index/reaction/r80/ https://www.wikidata.org/wiki/Q1945726 RXNO RXNO:0000149 Ireland-Claisen rearrangement RXNO:0000149 The enolisation and subsequent [3,3]-sigmatropic rearrangement of an allylic acetate to give a gamma,delta-unsaturated carboxylic acid. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A reaction in which one or more atoms are added to the molecular skeleton and a skeletal rearrangement occurs. RXNO RXNO:0000150 joining with rearrangement RXNO:0000150 A reaction in which one or more atoms are added to the molecular skeleton and a skeletal rearrangement occurs. https://orcid.org/0000-0001-5985-7429 The coupling and subsequent [3,3]-sigmatropic rearrangement of an allylic ether or allylic thioether or allylic amine and a ketene to give the corresponding gamma,delta-unsaturated carbonyl compound. RXNO RXNO:0000151 Bellus-Claisen rearrangement RXNO:0000151 The coupling and subsequent [3,3]-sigmatropic rearrangement of an allylic ether or allylic thioether or allylic amine and a ketene to give the corresponding gamma,delta-unsaturated carbonyl compound. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The coupling and subsequent [3,3]-sigmatropic rearrangement of an allylic alcohol and alpha,alpha-dialkoxy ethylamine to give a gamma,delta-unsaturated dialkyl amide. https://www.rsc.org/Merck-Index/reaction/r80/ RXNO RXNO:0000152 Eschenmoser-Claisen rearrangement RXNO:0000152 The coupling and subsequent [3,3]-sigmatropic rearrangement of an allylic alcohol and alpha,alpha-dialkoxy ethylamine to give a gamma,delta-unsaturated dialkyl amide. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The coupling and subsequent [3,3]-sigmatropic rearrangement of an allylic alcohol and trimethyl orthoacetate to give a gamma,delta-unsaturated alkyl ester. https://www.rsc.org/Merck-Index/reaction/r80/ RXNO RXNO:0000153 Johnson-Claisen rearrangement RXNO:0000153 The coupling and subsequent [3,3]-sigmatropic rearrangement of an allylic alcohol and trimethyl orthoacetate to give a gamma,delta-unsaturated alkyl ester. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The oxidation of a primary alcohol or secondary alcohol to an aldehyde or ketone respectively. Does not work with allylic or benzylic alcohols. https://www.rsc.org/Merck-Index/reaction/r426 RXNO RXNO:0000154 Swern oxidation RXNO:0000154 The oxidation of a primary alcohol or secondary alcohol to an aldehyde or ketone respectively. Does not work with allylic or benzylic alcohols. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The conversion of an alkyl chloride, alkyl bromide or alkyl sulfonate ester to an alkyl iodide by SN2 substitution. The reaction relies upon the equilibrium being pushed to completion by the precipitation. https://www.rsc.org/Merck-Index/reaction/r141/ RXNO RXNO:0000155 Finkelstein reaction RXNO:0000155 The conversion of an alkyl chloride, alkyl bromide or alkyl sulfonate ester to an alkyl iodide by SN2 substitution. The reaction relies upon the equilibrium being pushed to completion by the precipitation. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The derivatisation (for example with tosyl chloride) and subsequent rearrangement of a hydroxamic acid to give an isocyanate. https://www.rsc.org/Merck-Index/reaction/r259/ RXNO RXNO:0000156 Lossen rearrangement RXNO:0000156 The derivatisation (for example with tosyl chloride) and subsequent rearrangement of a hydroxamic acid to give an isocyanate. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The conversion of a primary nitroalkane or secondary nitroalkane to an aldehyde or ketone, respectively. https://www.rsc.org/Merck-Index/reaction/r297/ RXNO RXNO:0000157 Nef reaction RXNO:0000157 The conversion of a primary nitroalkane or secondary nitroalkane to an aldehyde or ketone, respectively. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The reaction of a doubly activated methylene compound that has at least one carbonyl substituent with an aryl azide to give a hydrazone. Usually there is concomitant cleaving and oxidation of one of the carbonyl substituents. RXNO RXNO:0000158 Japp-Klingemann reaction RXNO:0000158 The reaction of a doubly activated methylene compound that has at least one carbonyl substituent with an aryl azide to give a hydrazone. Usually there is concomitant cleaving and oxidation of one of the carbonyl substituents. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The formation of a quinoline from a primary aromatic amine and an alpha,beta-unsaturated carbonyl compound. Doebner-von Miller reaction Skraup-Doebner-von Miller quinoline synthesis RXNO RXNO:0000159 Doebner-Miller reaction RXNO:0000159 The formation of a quinoline from a primary aromatic amine and an alpha,beta-unsaturated carbonyl compound. https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The protection of an amine (often a peptide) as its 9H-fluoren-9-ylmethoxycarbonyl derivative. RXNO RXNO:0000160 Fmoc protection RXNO:0000160 The protection of an amine (often a peptide) as its 9H-fluoren-9-ylmethoxycarbonyl derivative. https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The cyclisation of a 1,4-dicarbonyl compound with another molecule to give a five-membered aromatic ring compound. RXNO RXNO:0000161 Usually this gives rise to a heterocycle. Paal-Knorr synthesis RXNO:0000161 The cyclisation of a 1,4-dicarbonyl compound with another molecule to give a five-membered aromatic ring compound. https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The cyclisation of a 1,4-dicarbonyl compound with an acid catalyst to give a furan. https://www.rsc.org/Merck-Index/reaction/r315/ RXNO RXNO:0000162 Paal-Knorr furan synthesis RXNO:0000162 The cyclisation of a 1,4-dicarbonyl compound with an acid catalyst to give a furan. https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The cyclisation of a 1,4-dicarbonyl compound with phosphorus pentasulfide to give a thiophene. RXNO RXNO:0000163 Paal-Knorr thiophene synthesis RXNO:0000163 The cyclisation of a 1,4-dicarbonyl compound with phosphorus pentasulfide to give a thiophene. https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The cyclisation of a 1,4-dicarbonyl compound with an amine to give a pyrrole. https://www.rsc.org/Merck-Index/reaction/r316/ RXNO RXNO:0000164 Merck Index says "ammonia or primary amines" Paal-Knorr pyrrole synthesis RXNO:0000164 The cyclisation of a 1,4-dicarbonyl compound with an amine to give a pyrrole. https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The coupling of an alcohol or amine with an acyl chloride to give an ester or amide. A two-phase solvent system is often used, to enable the acid generated during the reaction to be neutralised by the aqueous base, while the starting materials and products remain in the organic phase. https://www.rsc.org/Merck-Index/reaction/r392/ RXNO RXNO:0000165 Schotten-Baumann reaction RXNO:0000165 The coupling of an alcohol or amine with an acyl chloride to give an ester or amide. A two-phase solvent system is often used, to enable the acid generated during the reaction to be neutralised by the aqueous base, while the starting materials and products remain in the organic phase. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The elimination of a methylated amine from an alkylamine to form an olefin. The reaction proceeds via the quaternary ammonium salt. https://www.rsc.org/Merck-Index/reaction/r205/ exhaustive methylation RXNO Hofmann degradation RXNO:0000166 Hofmann elimination RXNO:0000166 The elimination of a methylated amine from an alkylamine to form an olefin. The reaction proceeds via the quaternary ammonium salt. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The esterification of a carboxylic acid with an alcohol. Various Lewis acids or Bronsted acids may be used as catalyst. Fischer esterification RXNO RXNO:0000167 Fischer-Speier esterification RXNO:0000167 The esterification of a carboxylic acid with an alcohol. Various Lewis acids or Bronsted acids may be used as catalyst. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The degradation of an alpha-hydroxy amide or an alpha,beta-unsaturated amide to the lower homologue aldehyde, especially in carbohydrate chemistry. The process proceeds via Hofmann degradation. Weerman degradation Weerman's reaction RXNO RXNO:0000168 Weerman reaction RXNO:0000168 The degradation of an alpha-hydroxy amide or an alpha,beta-unsaturated amide to the lower homologue aldehyde, especially in carbohydrate chemistry. The process proceeds via Hofmann degradation. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The reaction of ortho- or para-phenolic (or ortho- or para-anilinic) aldehydes or ketones with hydrogen peroxide to form bisphenols (or hydroxy anilines) and carboxylic acids. RXNO RXNO:0000169 Dakin reaction RXNO:0000169 The reaction of ortho- or para-phenolic (or ortho- or para-anilinic) aldehydes or ketones with hydrogen peroxide to form bisphenols (or hydroxy anilines) and carboxylic acids. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The reaction of a carboxylic acid with hydrazoic acid to give the lower homologue amine, with the loss of the terminal carbon atom. RXNO RXNO:0000170 Schmidt rearrangement, carboxylic acid RXNO:0000170 The reaction of a carboxylic acid with hydrazoic acid to give the lower homologue amine, with the loss of the terminal carbon atom. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The reaction of a ketone with hydrazoic acid with the insertion of an NH group between the carbonyl carbon and one of the R groups to form an amide. RXNO RXNO:0000171 Schmidt rearrangement, ketone RXNO:0000171 The reaction of a ketone with hydrazoic acid with the insertion of an NH group between the carbonyl carbon and one of the R groups to form an amide. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The reaction of a tertiary alcohol with hydrazoic acid with rearrangement to form an imide. RXNO RXNO:0000172 Schmidt rearrangement, tertiary alcohol RXNO:0000172 The reaction of a tertiary alcohol with hydrazoic acid with rearrangement to form an imide. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The reaction of an alkene with hydrazoic acid with rearrangement to form an imide. RXNO RXNO:0000173 Schmidt rearrangement, alkene RXNO:0000173 The reaction of an alkene with hydrazoic acid with rearrangement to form an imide. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The [2,3]-sigmatropic rearrangement of a benzyl quaternary ammonium salt to form an aniline. RXNO RXNO:0000174 Sommelet-Hauser rearrangement RXNO:0000174 The [2,3]-sigmatropic rearrangement of a benzyl quaternary ammonium salt to form an aniline. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The reaction of an amino acid with an acid anhydride to give an alpha-acylamido ketone. The reaction proceeds via the mixed anhydride and an oxazolone; the product is always racemic. RXNO RXNO:0000175 Dakin-West reaction RXNO:0000175 The reaction of an amino acid with an acid anhydride to give an alpha-acylamido ketone. The reaction proceeds via the mixed anhydride and an oxazolone; the product is always racemic. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The cleavage of an oxime to the corresponding nitrile and an alkyl halide. This reaction is related to the Beckmann rearrangement, and occurs when the R group that is anti to the oxime hydroxyl is quaternary. RXNO RXNO:0000176 Beckmann fragmentation RXNO:0000176 The cleavage of an oxime to the corresponding nitrile and an alkyl halide. This reaction is related to the Beckmann rearrangement, and occurs when the R group that is anti to the oxime hydroxyl is quaternary. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The transfer of a hydrogen or halogen atom from a haloalkane to an alkene, giving the chain-extended halogenated alkane. Kharasch addition reaction RXNO RXNO:0000177 Kharasch reaction RXNO:0000177 The transfer of a hydrogen or halogen atom from a haloalkane to an alkene, giving the chain-extended halogenated alkane. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The allylic oxidation of an alkene with a peroxy ester or a peroxide to give the corresponding allylic alcohol derivative. The catalyst is a copper compound. RXNO RXNO:0000178 Kharasch-Sosnovsky reaction RXNO:0000178 The allylic oxidation of an alkene with a peroxy ester or a peroxide to give the corresponding allylic alcohol derivative. The catalyst is a copper compound. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The oxidation of a phenol to give a (predominantly para) diphenol using potassium persulfate. RXNO RXNO:0000179 Elbs persulfate oxidation, phenol variant RXNO:0000179 The oxidation of a phenol to give a (predominantly para) diphenol using potassium persulfate. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The oxidation of a methyl-substituted aromatic compound to the corresponding benzaldehyde using potassium persulfate. RXNO RXNO:0000180 Elbs persulfate oxidation, tolyl variant RXNO:0000180 The oxidation of a methyl-substituted aromatic compound to the corresponding benzaldehyde using potassium persulfate. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The oxidation of an aromatic amine to give a (predominantly ortho) amino aryl sulfate using potassium persulfate followed by hydrolysis to yield the corresponding aminophenol. https://www.rsc.org/Merck-Index/reaction/r59/ RXNO RXNO:0000181 Boyland-Sims oxidation RXNO:0000181 The oxidation of an aromatic amine to give a (predominantly ortho) amino aryl sulfate using potassium persulfate followed by hydrolysis to yield the corresponding aminophenol. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The (predominantly ortho) carboxylation of a phenoxide. https://www.rsc.org/Merck-Index/reaction/r239/ RXNO RXNO:0000182 Kolbe-Schmitt reaction RXNO:0000182 The (predominantly ortho) carboxylation of a phenoxide. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The reaction between an alpha-halocarbonyl compound and a trialkyl phosphite to give an enol phosphate. https://www.rsc.org/Merck-Index/reaction/r329/ RXNO RXNO:0000183 not clear why this is where it is and not a sibling of the Arbuzov reaction (2014-02-17) Perkow reaction RXNO:0000183 The reaction between an alpha-halocarbonyl compound and a trialkyl phosphite to give an enol phosphate. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The oxidation of a primary or secondary alcohol to the corresponding aldehyde or ketone respectively using dimethyl sulfoxide, 1,3-dicyclohexylcarbodiimide and acid. The reaction proceeds via an alkoxysulfonium ylide. https://www.rsc.org/Merck-Index/reaction/r335/ Moffatt oxidation RXNO RXNO:0000184 Pfitzner-Moffatt oxidation RXNO:0000184 The oxidation of a primary or secondary alcohol to the corresponding aldehyde or ketone respectively using dimethyl sulfoxide, 1,3-dicyclohexylcarbodiimide and acid. The reaction proceeds via an alkoxysulfonium ylide. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The conversion of an aryl alkyl ketone to an amide and/or an ammonium salt of a carboxylic acid using ammonium polysulfide. The carbonyl group of the product is always at the end of the alkyl chain. RXNO RXNO:0000185 Willgerodt reaction RXNO:0000185 The conversion of an aryl alkyl ketone to an amide and/or an ammonium salt of a carboxylic acid using ammonium polysulfide. The carbonyl group of the product is always at the end of the alkyl chain. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The conversion of an aryl alkyl ketone to an amide using sulfur and dry ammonia or a primary or secondary amine. The amide carbonyl group is always at the end of the alkyl chain. https://www.rsc.org/Merck-Index/reaction/r466/ RXNO RXNO:0000186 Willgerodt-Kindler reaction RXNO:0000186 The conversion of an aryl alkyl ketone to an amide using sulfur and dry ammonia or a primary or secondary amine. The amide carbonyl group is always at the end of the alkyl chain. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The formation of an ester from two aldehydes via a disproportionation process using a metal alkoxide to oxidise one aldehyde and reduce the other. https://www.rsc.org/Merck-Index/reaction/r433/ RXNO RXNO:0000187 Tishchenko reaction RXNO:0000187 The formation of an ester from two aldehydes via a disproportionation process using a metal alkoxide to oxidise one aldehyde and reduce the other. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The reaction between a methylene ketone and a polynitro aromatic compound. https://www.rsc.org/Merck-Index/reaction/r482/ RXNO RXNO:0000188 Zimmermann reaction RXNO:0000188 The reaction between a methylene ketone and a polynitro aromatic compound. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The rearrangement of the sulfonic ester of a ketoxime in base to give an alpha-amino ketone. https://www.rsc.org/Merck-Index/reaction/r296/ RXNO RXNO:0000189 Neber rearrangement RXNO:0000189 The rearrangement of the sulfonic ester of a ketoxime in base to give an alpha-amino ketone. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 true RXNO:0000190 A coupling reaction of an aldehyde to an allyl, vinyl or aryl halide or triflate in the presence of chromium(II). It is catalysed by nickel. Nozaki reaction Nozaki-Hiyama-Kishi coupling Nozaki-Kishi reaction RXNO RXNO:0000191 Nozaki-Hiyama-Kishi reaction RXNO:0000191 A coupling reaction of an aldehyde to an allyl, vinyl or aryl halide or triflate in the presence of chromium(II). It is catalysed by nickel. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A reaction in which an aryl halide or aryl triflate reacts with a primary or secondary amine in the presence of base to give a secondary or tertiary amine. It is catalysed by a palladium catalyst. Buchwald-Hartwig reaction RXNO RXNO:0000192 Buchwald-Hartwig amination RXNO:0000192 A reaction in which an aryl halide or aryl triflate reacts with a primary or secondary amine in the presence of base to give a secondary or tertiary amine. It is catalysed by a palladium catalyst. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A carbon-carbon coupling reaction where an organosilane reacts with an organic halide or triflate. It is catalysed by a palladium or nickel complex. Hiyama cross-coupling RXNO RXNO:0000193 Hiyama coupling RXNO:0000193 A carbon-carbon coupling reaction where an organosilane reacts with an organic halide or triflate. It is catalysed by a palladium or nickel complex. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The 1,2-rearrangement of an alpha-methylene ammonium salt or alpha-methylene sulfonium salt to an amine or sulfide in the presence of strong base. RXNO RXNO:0000194 Stevens rearrangement RXNO:0000194 The 1,2-rearrangement of an alpha-methylene ammonium salt or alpha-methylene sulfonium salt to an amine or sulfide in the presence of strong base. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The 1,2-rearrangement of an alpha-methylene ammonium salt to an amine in the presence of strong base. RXNO RXNO:0000195 Stevens rearrangement, ammonium RXNO:0000195 The 1,2-rearrangement of an alpha-methylene ammonium salt to an amine in the presence of strong base. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The 1,2-rearrangement of an alpha-methylene sulfonium salt to a sulfide in the presence of strong base. RXNO RXNO:0000196 Stevens rearrangement, sulfonium RXNO:0000196 The 1,2-rearrangement of an alpha-methylene sulfonium salt to a sulfide in the presence of strong base. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A [3,3]-sigmatropic rearrangement where an aza-1,5-hexadiene rearranges to form an aza-1,5-hexadiene. RXNO RXNO:0000197 aza-Cope rearrangement RXNO:0000197 A [3,3]-sigmatropic rearrangement where an aza-1,5-hexadiene rearranges to form an aza-1,5-hexadiene. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The rearrangement of a 2-aza-1,5-hexadiene to form an imine. RXNO RXNO:0000198 2-aza-Cope rearrangement RXNO:0000198 The rearrangement of a 2-aza-1,5-hexadiene to form an imine. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The rearrangement of a 3-aza-1,5-hexadiene to form a delta,epsilon-unsaturated imine. amino-Claisen rearrangement aza-Claisen rearrangement RXNO RXNO:0000199 This is the reverse of the 1-aza-Cope rearrangement. 3-aza-Cope rearrangement RXNO:0000199 The rearrangement of a 3-aza-1,5-hexadiene to form a delta,epsilon-unsaturated imine. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The rearrangement of a delta,epsilon-unsaturated imine to form a 3-aza-1,5-hexadiene. RXNO RXNO:0000200 This is the reverse of the 3-aza-Cope rearrangement. 1-aza-Cope rearrangement RXNO:0000200 The rearrangement of a delta,epsilon-unsaturated imine to form a 3-aza-1,5-hexadiene. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The rearrangement of an oxazolyl carbonate to a C-carboxyazlactone. RXNO RXNO:0000201 Steglich rearrangement RXNO:0000201 The rearrangement of an oxazolyl carbonate to a C-carboxyazlactone. RSC:jrw https://orcid.org/0000-0001-5985-7429 A reaction in which the number of rings in a molecule stays the same but the connectivity of the atoms in at least one ring changes. RXNO RXNO:0000202 ring rearrangement RXNO:0000202 A reaction in which the number of rings in a molecule stays the same but the connectivity of the atoms in at least one ring changes. https://orcid.org/0000-0001-5985-7429 A reaction in which a protecting group is modified by converting it into a functional group. NAMERXN:6 RXNO RXNO:0000203 deprotection reaction RXNO:0000203 A reaction in which a protecting group is modified by converting it into a functional group. https://orcid.org/0000-0001-5985-7429 A joining reaction in which two carbon-carbon multiple bonds are redistributed among two fragments. The reaction is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of a low-MW alkene. metathesis multiple bond metathesis RXNO RXNO:0000204 multiple-bond metathesis RXNO:0000204 A joining reaction in which two carbon-carbon multiple bonds are redistributed among two fragments. The reaction is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of a low-MW alkene. https://orcid.org/0000-0001-5985-7429 A planned reaction step in which the product has fewer rings than the reactants. ring opening selective ring opening RXNO RXNO:0000205 ring breaking RXNO:0000205 A planned reaction step in which the product has fewer rings than the reactants. https://orcid.org/0000-0001-5985-7429 A planned reaction step in which an existing ring is reduced in size. RXNO RXNO:0000206 ring contraction RXNO:0000206 A planned reaction step in which an existing ring is reduced in size. https://orcid.org/0000-0001-5985-7429 An addition reaction between a carbonyl compound, an inorganic cyanide and an ammonium salt, followed by hydrolysis, to give an alpha-amino carboxylic acid. RXNO RXNO:0000207 Strecker reaction RXNO:0000207 An addition reaction between a carbonyl compound, an inorganic cyanide and an ammonium salt, followed by hydrolysis, to give an alpha-amino carboxylic acid. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The [3,3]-sigmatropic rearrangement, and subsequent re-aromatisation, of an allyl aryl ether to give an ortho-allyl phenol. RXNO RXNO:0000208 aromatic Claisen rearrangement RXNO:0000208 The [3,3]-sigmatropic rearrangement, and subsequent re-aromatisation, of an allyl aryl ether to give an ortho-allyl phenol. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The acid-catalysed cyclisation of a divinylketone to give a cyclopentenone. https://www.rsc.org/Merck-Index/reaction/r295/ Nazarov cyclization RXNO RXNO:0000209 Nazarov cyclisation RXNO:0000209 The acid-catalysed cyclisation of a divinylketone to give a cyclopentenone. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The stereospecific oxidation of a (phenyldimethylsilyl)alkane to the corresponding alcohol using bromine, usually generated in situ from potassium bromide and peracetic acid. https://www.rsc.org/Merck-Index/reaction/r150/ Fleming oxidation Tamao-Fleming oxidation RXNO RXNO:0000210 Fleming-Tamao oxidation RXNO:0000210 The stereospecific oxidation of a (phenyldimethylsilyl)alkane to the corresponding alcohol using bromine, usually generated in situ from potassium bromide and peracetic acid. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The stereospecific oxidation of a (halosilyl)alkane to the corresponding alcohol using potassium fluoride and hydrogen peroxide. https://www.rsc.org/Merck-Index/reaction/r150/ Tamao-Kumada oxidation RXNO RXNO:0000211 Tamao oxidation RXNO:0000211 The stereospecific oxidation of a (halosilyl)alkane to the corresponding alcohol using potassium fluoride and hydrogen peroxide. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A carbon-carbon coupling reaction in which an aldehyde or ketone reacts with allyltrimethylsilane to form a homoallylic alcohol. RXNO RXNO:0000212 Sakurai reaction, aldehyde or ketone RXNO:0000212 A carbon-carbon coupling reaction in which an aldehyde or ketone reacts with allyltrimethylsilane to form a homoallylic alcohol. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A carbon-carbon coupling reaction in which an enone reacts with allyltrimethylsilane to form a delta,epsilon-unsaturated carbonyl compound. RXNO RXNO:0000213 Sakurai reaction, enone RXNO:0000213 A carbon-carbon coupling reaction in which an enone reacts with allyltrimethylsilane to form a delta,epsilon-unsaturated carbonyl compound. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A carbon-carbon coupling reaction in which an acid chloride reacts with allyltrimethylsilane to form a gamma,delta-unsaturated ketone. RXNO RXNO:0000214 Sakurai reaction, acid chloride RXNO:0000214 A carbon-carbon coupling reaction in which an acid chloride reacts with allyltrimethylsilane to form a gamma,delta-unsaturated ketone. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A carbon-carbon coupling reaction in which an acetal or ketal reacts with allyltrimethylsilane to form a homoallylic ether. RXNO RXNO:0000215 Sakurai reaction, acetal or ketal RXNO:0000215 A carbon-carbon coupling reaction in which an acetal or ketal reacts with allyltrimethylsilane to form a homoallylic ether. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A carbon-carbon coupling reaction in which an imine reacts with allyltrimethylsilane to form a homoallylic amine. RXNO RXNO:0000216 imine Sakurai reaction RXNO:0000216 A carbon-carbon coupling reaction in which an imine reacts with allyltrimethylsilane to form a homoallylic amine. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A ring-breaking reaction in which an epoxide reacts with allyltrimethylsilane to form a hydroxy alkene. RXNO RXNO:0000217 Sakurai reaction, epoxide RXNO:0000217 A ring-breaking reaction in which an epoxide reacts with allyltrimethylsilane to form a hydroxy alkene. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The disproportionation of a non-enolisable aldehyde to the corresponding carboxylic acid and alcohol. The reaction is base-catalysed. https://www.rsc.org/Merck-Index/reaction/r71/ RXNO RXNO:0000218 Cannizzaro reaction RXNO:0000218 The disproportionation of a non-enolisable aldehyde to the corresponding carboxylic acid and alcohol. The reaction is base-catalysed. RSC:db https://orcid.org/0000-0002-4077-4719 The reaction between two different non-enolisable aldehydes to give a carboxylic acid and an alcohol. The reaction is base-catalysed. https://www.rsc.org/Merck-Index/reaction/r71/ RXNO RXNO:0000219 crossed Cannizzaro reaction RXNO:0000219 The reaction between two different non-enolisable aldehydes to give a carboxylic acid and an alcohol. The reaction is base-catalysed. RSC:db https://orcid.org/0000-0002-4077-4719 The conversion of a sulfoxide with an alpha-hydrogen to an alpha-substituted thioether. The reaction is usually performed with an acid anhydride or acyl halide. Pummerer methyl sulfoxide rearrangement RXNO RXNO:0000220 Pummerer rearrangement RXNO:0000220 The conversion of a sulfoxide with an alpha-hydrogen to an alpha-substituted thioether. The reaction is usually performed with an acid anhydride or acyl halide. RSC:db https://orcid.org/0000-0002-4077-4719 The reaction of a tertiary amine oxide with an anhydride or acyl chloride to give an N,N-disubstituted acetamide and an aldehyde. RXNO RXNO:0000221 Polonovski reaction RXNO:0000221 The reaction of a tertiary amine oxide with an anhydride or acyl chloride to give an N,N-disubstituted acetamide and an aldehyde. RSC:db https://orcid.org/0000-0002-4077-4719 The reaction of a tertiary amine oxide with trifluoroacetic anhydride to give an N,N-disubstituted acetamide and an aldehyde. Potier-Polonovski reaction RXNO RXNO:0000222 Polonovski-Potier reaction RXNO:0000222 The reaction of a tertiary amine oxide with trifluoroacetic anhydride to give an N,N-disubstituted acetamide and an aldehyde. RSC:db https://orcid.org/0000-0002-4077-4719 The alkylation of a tertiary amine with an alkyl halide to the corresponding ammonium salt. RXNO:0000375 https://www.rsc.org/Merck-Index/reaction/r275/ Menschutkin reaction RXNO RXNO:0000223 Menshutkin reaction RXNO:0000223 The alkylation of a tertiary amine with an alkyl halide to the corresponding ammonium salt. RSC:db https://orcid.org/0000-0002-4077-4719 The deamination and decarboxylation of amino acids to imines and then to aldehydes or ketones, in the presence of a carbonyl compound (especially an alpha,beta-dicarbonyl compound or a reducing sugar such as glucose). The reaction is involved in the generation of meat aromas/flavours in cooking. RXNO RXNO:0000224 Strecker degradation RXNO:0000224 The deamination and decarboxylation of amino acids to imines and then to aldehydes or ketones, in the presence of a carbonyl compound (especially an alpha,beta-dicarbonyl compound or a reducing sugar such as glucose). The reaction is involved in the generation of meat aromas/flavours in cooking. RSC:db https://orcid.org/0000-0002-4077-4719 The allylic or benzylic bromination of hydrocarbons using an N-bromoimide and a radical initiator, to give an allylic or benzylic bromide. Wohl-Ziegler reaction RXNO RXNO:0000225 Wohl-Ziegler bromination RXNO:0000225 The allylic or benzylic bromination of hydrocarbons using an N-bromoimide and a radical initiator, to give an allylic or benzylic bromide. RSC:db https://orcid.org/0000-0002-4077-4719 The reduction of an aldehyde or ketone to the corresponding methylene compound, using hydrazine hydrate and a base. RXNO RXNO:0000226 Wolff-Kishner reduction RXNO:0000226 The reduction of an aldehyde or ketone to the corresponding methylene compound, using hydrazine hydrate and a base. RSC:db https://orcid.org/0000-0002-4077-4719 The reduction of an aldehyde or ketone to the corresponding methylene compound, using hydrazine hydrate and a base in refluxing ethylene glycol. Huang-Minlon modification RXNO RXNO:0000227 Wolff-Kishner reduction, Huang-Minlon modification RXNO:0000227 The reduction of an aldehyde or ketone to the corresponding methylene compound, using hydrazine hydrate and a base in refluxing ethylene glycol. RSC:db https://orcid.org/0000-0002-4077-4719 The reduction of an ester to the corresponding alcohol, using sodium methoxide in dry methanol. Zemplen procedure RXNO RXNO:0000228 Zemplen transesterification RXNO:0000228 The reduction of an ester to the corresponding alcohol, using sodium methoxide in dry methanol. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The rearrangement of an O-alkenyl acetal to give the corresponding beta-alkoxy carbonyl compound. Ferrier reaction RXNO RXNO:0000229 Ferrier rearrangement RXNO:0000229 The rearrangement of an O-alkenyl acetal to give the corresponding beta-alkoxy carbonyl compound. https://orcid.org/0000-0002-4077-4719 The rearrangement of an O-alkenyl hemiaminal ether to give the corresponding beta-amino carbonyl compound. aza-Ferrier reaction RXNO RXNO:0000230 aza-Ferrier rearrangement RXNO:0000230 The rearrangement of an O-alkenyl hemiaminal ether to give the corresponding beta-amino carbonyl compound. https://orcid.org/0000-0002-4077-4719 A joining reaction where an N=C system with an allylic hydrogen reacts with a compound containing a multiple bond (an enophile) to form a substituted alkene. RXNO RXNO:0000231 aza-ene reaction RXNO:0000231 A joining reaction where an N=C system with an allylic hydrogen reacts with a compound containing a multiple bond (an enophile) to form a substituted alkene. https://orcid.org/0000-0001-5985-7429 The alkylation of an amine with a boronic acid and an aldehyde to give a substituted amine. Petasis three-component coupling RXNO RXNO:0000232 Petasis reaction RXNO:0000232 The alkylation of an amine with a boronic acid and an aldehyde to give a substituted amine. RSC:db A rearrangement of a furfuryl alcohol derivative to a dihydropyranone, from which monosaccharides may be synthesised. RXNO RXNO:0000233 Achmatowicz rearrangement RXNO:0000233 A rearrangement of a furfuryl alcohol derivative to a dihydropyranone, from which monosaccharides may be synthesised. RSC:db A rearrangement of a furfuryl amine derivative to a tetrahydropyridinone. RXNO RXNO:0000234 aza-Achmatowicz rearrangement RXNO:0000234 A rearrangement of a furfuryl amine derivative to a tetrahydropyridinone. RSC:db A carbon-carbon coupling reaction between a nitroalkane and an imine to give a beta-amino nitroalkane. RXNO RXNO:0000235 aza-Henry reaction RXNO:0000235 A carbon-carbon coupling reaction between a nitroalkane and an imine to give a beta-amino nitroalkane. RSC:db A three-component coupling of a beta-keto ester, an aldehyde and urea to give a 3,4-dihydropyrimidinone. https://www.rsc.org/Merck-Index/reaction/r43/ Biginelli condensation Biginelli pyrimidone synthesis Biginelli three-component reaction RXNO RXNO:0000236 Biginelli reaction RXNO:0000236 A three-component coupling of a beta-keto ester, an aldehyde and urea to give a 3,4-dihydropyrimidinone. RSC:db The coupling of an alpha-bromo ester with a nitrile to give a beta-ketoester, in the presence of zinc. RXNO RXNO:0000237 Blaise reaction RXNO:0000237 The coupling of an alpha-bromo ester with a nitrile to give a beta-ketoester, in the presence of zinc. RSC:db The substitution of an amine with a nucleophile using a pyrylium salt. RXNO RXNO:0000238 Katritzky pyrylium-pyridinium method RXNO:0000238 The substitution of an amine with a nucleophile using a pyrylium salt. https://orcid.org/0000-0002-4077-4719 The rearrangement of a 3-aza-4-metalla-1,5-hexadiene to form a delta,epsilon-unsaturated metallaimine. RXNO RXNO:0000239 metalla-aza-Claisen rearrangement RXNO:0000239 The rearrangement of a 3-aza-4-metalla-1,5-hexadiene to form a delta,epsilon-unsaturated metallaimine. https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 The cyclisation of an ene-diyne to give a 1,4-diradical cyclohexatriene. The diradical usually aromatises. https://www.rsc.org/Merck-Index/reaction/r37/ Bergman cyclization Bergman reaction Masamune-Bergman cyclisation Masamune-Bergman cyclization RXNO RXNO:0000240 Bergman cyclisation RXNO:0000240 The cyclisation of an ene-diyne to give a 1,4-diradical cyclohexatriene. The diradical usually aromatises. https://orcid.org/0000-0002-4077-4719 A conjugate addition reaction where a carbon nucleophile adds to an alpha,beta-unsaturated nitro compound. RXNO RXNO:0000241 nitro-Michael reaction RXNO:0000241 A conjugate addition reaction where a carbon nucleophile adds to an alpha,beta-unsaturated nitro compound. https://orcid.org/0000-0002-4077-4719 The homogeneous asymmetric catalytic hydrogenation of a C=C double bond using a ruthenium(II) BINAP catalyst. Noyori hydrogenation, alkene RXNO RXNO:0000242 Noyori asymmetric hydrogenation, alkene RXNO:0000242 The homogeneous asymmetric catalytic hydrogenation of a C=C double bond using a ruthenium(II) BINAP catalyst. https://orcid.org/0000-0002-4077-4719 The homogeneous asymmetric catalytic hydrogenation of a carbonyl bond using a ruthenium(II) BINAP catalyst. Noyori hydrogenation, carbonyl RXNO RXNO:0000243 Noyori asymmetric hydrogenation, carbonyl RXNO:0000243 The homogeneous asymmetric catalytic hydrogenation of a carbonyl bond using a ruthenium(II) BINAP catalyst. https://orcid.org/0000-0002-4077-4719 The reaction between an isonitrile, a carboxylic acid and aldehyde or ketone to give an alpha-acyloxy amide. RXNO RXNO:0000244 Passerini reaction RXNO:0000244 The reaction between an isonitrile, a carboxylic acid and aldehyde or ketone to give an alpha-acyloxy amide. https://orcid.org/0000-0002-4077-4719 A joining reaction in which two carbon-carbon double bonds in the same molecule are redistributed to give a cycloalkene. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of a low-MW alkene. RCM ring closing alkene metathesis ring closing metathesis ring closing olefin metathesis ring-closing alkene metathesis ring-closing olefin metathesis RXNO RXNO:0000245 ring-closing metathesis RXNO:0000245 A joining reaction in which two carbon-carbon double bonds in the same molecule are redistributed to give a cycloalkene. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of a low-MW alkene. https://orcid.org/0000-0002-4077-4719 A joining reaction, the objective of which is that a large number of monomers react together to produce a polymer consisting of repeating units. polymerisation polymerization polymerization reaction RXNO RXNO:0000246 polymerisation reaction RXNO:0000246 A joining reaction, the objective of which is that a large number of monomers react together to produce a polymer consisting of repeating units. rsc:db A joining reaction in which two carbon-carbon double bonds are redistributed among two fragments, i.e. two alkenes. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of ring strain in the cycloalkene. ROMP ring-opening metathesis polymerization RXNO RXNO:0000247 ring-opening metathesis polymerisation RXNO:0000247 A joining reaction in which two carbon-carbon double bonds are redistributed among two fragments, i.e. two alkenes. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of ring strain in the cycloalkene. https://orcid.org/0000-0002-4077-4719 rsc:db An adaptation of the Claisen rearrangement that transforms a beta-keto allyl ester into a gamma,delta-allyl ketone. It uses base and high temperature or milder conditions with a ruthenium or palladium complex as catalyst. https://www.rsc.org/Merck-Index/reaction/r72/ Kimel-Cope rearrangement RXNO RXNO:0000248 Carroll rearrangement RXNO:0000248 An adaptation of the Claisen rearrangement that transforms a beta-keto allyl ester into a gamma,delta-allyl ketone. It uses base and high temperature or milder conditions with a ruthenium or palladium complex as catalyst. RSC:db A Mitsunobu reaction, where an alcohol is converted to something else with inversion at the stereocentre, using diphenylphosphoryl azide. RXNO RXNO:0000249 Bose-Mitsunobu reaction RXNO:0000249 A Mitsunobu reaction, where an alcohol is converted to something else with inversion at the stereocentre, using diphenylphosphoryl azide. RSC:db The rearrangement of a 2-bromoalkene into an alkyne, mediated by strong base. https://www.rsc.org/Merck-Index/reaction/r161/ https://www.wikidata.org/wiki/Q573664 RXNO RXNO:0000250 Fritsch-Buttenberg-Wiechell rearrangement RXNO:0000250 The rearrangement of a 2-bromoalkene into an alkyne, mediated by strong base. RSC:db A carbon-carbon coupling reaction where an aldehyde reacts with a phosphonium salt to give a Z-iodoalkene. The reaction is mediated by sodium or potassium hexamethyldisilazide. RXNO RXNO:0000251 Stork-Wittig olefination RXNO:0000251 A carbon-carbon coupling reaction where an aldehyde reacts with a phosphonium salt to give a Z-iodoalkene. The reaction is mediated by sodium or potassium hexamethyldisilazide. RSC:db The reduction of a 2-nitrobiaryl compound to give a carbazole. RXNO RXNO:0000252 Cadogan carbazole synthesis RXNO:0000252 The reduction of a 2-nitrobiaryl compound to give a carbazole. doi:10.1039/JR9650004831 https://orcid.org/0000-0002-4077-4719 The arylation of an arylamine mediated by isopentyl nitrite. RXNO RXNO:0000253 Cadogan coupling RXNO:0000253 The arylation of an arylamine mediated by isopentyl nitrite. doi:10.1039/b409373a https://orcid.org/0000-0002-4077-4719 The reaction between a 1,9-diformyldipyrromethane and a dipyrromethane to give a porphodimethene. RXNO RXNO:0000254 MacDonald condensation RXNO:0000254 The reaction between a 1,9-diformyldipyrromethane and a dipyrromethane to give a porphodimethene. doi:10.1039/a908784b https://orcid.org/0000-0002-4077-4719 The carbon-carbon homocoupling reaction of a pair of alkyne molecules using a borane and iodine. The reaction proceeds via a borane intermediate. RXNO RXNO:0000255 Zweifel diene synthesis RXNO:0000255 The carbon-carbon homocoupling reaction of a pair of alkyne molecules using a borane and iodine. The reaction proceeds via a borane intermediate. https://orcid.org/0000-0002-4077-4719 isbn:9780521096430 The oxidation of a primary alcohol to an aldehyde or a secondary alcohol to a ketone using the Dess-Martin periodinane. https://www.rsc.org/Merck-Index/reaction/r107/ https://www.wikidata.org/wiki/Q28455131 Dess-Martin periodinane oxidation RXNO RXNO:0000256 Dess-Martin oxidation RXNO:0000256 The oxidation of a primary alcohol to an aldehyde or a secondary alcohol to a ketone using the Dess-Martin periodinane. https://orcid.org/0000-0001-5985-7429 The oxidative cleavage of an alpha,beta-diol using lead tetraacetate to give the corresponding carbonyl compounds. https://www.rsc.org/Merck-Index/reaction/r96/ https://www.wikidata.org/wiki/Q30693026 Criegee glycol cleavage Criegee reaction RXNO RXNO:0000257 Criegee oxidation RXNO:0000257 The oxidative cleavage of an alpha,beta-diol using lead tetraacetate to give the corresponding carbonyl compounds. https://orcid.org/0000-0001-5985-7429 A ring formation reaction where an alkene reacts with a dihalomethane in the presence of a metal atom or metal complexes to form a cyclopropane. The traditional reaction uses a zinc-copper couple and diiodomethane. https://www.rsc.org/Merck-Index/reaction/r400/ https://www.wikidata.org/wiki/Q903776 Simmons-Smith cyclopropanation RXNO RXNO:0000258 Simmons-Smith reaction RXNO:0000258 A ring formation reaction where an alkene reacts with a dihalomethane in the presence of a metal atom or metal complexes to form a cyclopropane. The traditional reaction uses a zinc-copper couple and diiodomethane. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 Any of a family of sigmatropic rearrangements that involve the migration of a group on an electronegative atom (O or N) to a carbon atom. RXNO RXNO:0000259 Wittig rearrangement RXNO:0000259 Any of a family of sigmatropic rearrangements that involve the migration of a group on an electronegative atom (O or N) to a carbon atom. https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 rsc:db A base-mediated 1,2-sigmatropic rearrangement of an ether to give an alcohol. 1,2-Wittig rearrangement [1,2] Wittig rearrangement RXNO RXNO:0000260 [1,2]-Wittig rearrangement RXNO:0000260 A base-mediated 1,2-sigmatropic rearrangement of an ether to give an alcohol. rsc:db A base-mediated 2,3-sigmatropic rearrangement of an allyl ether to give a homoallylic alcohol. 2,3-Wittig rearrangement [2,3] Wittig rearrangement RXNO RXNO:0000261 [2,3]-Wittig rearrangement RXNO:0000261 A base-mediated 2,3-sigmatropic rearrangement of an allyl ether to give a homoallylic alcohol. rsc:db A base-mediated 1,2-sigmatropic rearrangement of a tertiary amine to give a secondary amine. 1,2-aza-Wittig rearrangement [1,2] aza-Wittig rearrangement RXNO RXNO:0000262 [1,2]-aza-Wittig rearrangement RXNO:0000262 A base-mediated 1,2-sigmatropic rearrangement of a tertiary amine to give a secondary amine. rsc:db A base-mediated 2,3-sigmatropic rearrangement of an activated tertiary allyl amine, to give a secondary homoallylic amine. 2,3-aza-Wittig rearrangement [2,3] aza-Wittig rearrangement RXNO RXNO:0000263 [2,3]-aza-Wittig rearrangement RXNO:0000263 A base-mediated 2,3-sigmatropic rearrangement of an activated tertiary allyl amine, to give a secondary homoallylic amine. rsc:db A carbon-carbon coupling of an imine to an activated alkene in the presence of a nucleophilic base to give an allylic amine. aza-Morita-Baylis-Hillman reaction RXNO RXNO:0000264 aza-Baylis-Hillman reaction RXNO:0000264 A carbon-carbon coupling of an imine to an activated alkene in the presence of a nucleophilic base to give an allylic amine. rsc:db Reaction of a carbonyl compound with a phosphazene to give an imine. RXNO RXNO:0000265 aza-Wittig reaction RXNO:0000265 Reaction of a carbonyl compound with a phosphazene to give an imine. rsc:db An oxidation reaction involving Fenton's reagent. RXNO:0000267 Fenton's reaction RXNO RXNO:0000266 Fenton reaction RXNO:0000266 An oxidation reaction involving Fenton's reagent. https://orcid.org/0000-0001-5985-7429 true RXNO:0000267 A ring-forming reaction between two equivalents of a beta-ketoester, an aldehyde and ammonia (or an ammonium salt), to give a dihydropyridine. The dihydropyridine can be oxidised to a pyridine using an oxidising agent. Hantzsch dihydropyridine synthesis RXNO RXNO:0000268 Hantzsch pyridine synthesis RXNO:0000268 A ring-forming reaction between two equivalents of a beta-ketoester, an aldehyde and ammonia (or an ammonium salt), to give a dihydropyridine. The dihydropyridine can be oxidised to a pyridine using an oxidising agent. rsc:db A [3+2] cycloaddition reaction between an azide and an alkyne to give a 1,2,3-triazole, needing only heat to proceed. Huisgen cycloaddition Huisgen reaction Huisgen's 1,3-dipolar cycloaddition "click" reaction 'click' reaction alkyne-azide Huisgen cycloaddition alkyne-azide Huisgen reaction azide-alkyne Huisgen cycloaddition azide-alkyne Huisgen reaction azide-alkyne click reaction click reaction RXNO RXNO:0000269 Note: The term "click reaction" was originally used in a broader sense to refer to any coupling that took place cleanly and quickly in quantitative yield, but it now always seems to be used in this narrower sense. alkyne-azide click reaction RXNO:0000269 A [3+2] cycloaddition reaction between an azide and an alkyne to give a 1,2,3-triazole, needing only heat to proceed. rsc:db A [3+2] cycloaddition reaction between an azide and an alkyne to give a 1,2,3-triazole as a single regioisomer. CuAAC copper(I)-catalysed alkyne-azide cycloaddition copper(I)-catalysed azide-alkyne click reaction copper(I)-catalysed azide-alkyne cycloaddition copper(I)-catalyzed alkyne-azide cycloaddition copper(I)-catalyzed azide-alkyne click reaction copper(I)-catalyzed azide-alkyne cycloaddition RXNO RXNO:0000270 Commonly described as a variant of the (uncatalyzed) alkyne-azide click reaction, the mechanism of reaction is different, and thus formally it is not a 1,3-dipolar cycloaddition. [rsc:db] copper(I)-catalyzed azide-alkyne cycloaddition RXNO:0000270 A [3+2] cycloaddition reaction between an azide and an alkyne to give a 1,2,3-triazole as a single regioisomer. RSC:db A process in which carbon monoxide and hydrogen ('syngas') are converted into various liquid hydrocarbons. Fischer-Tropsch reaction Fischer-Tropsch synthesis RXNO RXNO:0000271 Fischer-Tropsch process RXNO:0000271 A process in which carbon monoxide and hydrogen ('syngas') are converted into various liquid hydrocarbons. rsc:db The reaction of hydrogen and carbon monoxide with an alkene, to give an aldehyde, catalysed by a rhodium or cobalt catalyst. The process is equivalent to the formal addition of the H-C bond of formaldehyde across the double bond of an alkene. RXNO RXNO:0000272 hydroformylation RXNO:0000272 The reaction of hydrogen and carbon monoxide with an alkene, to give an aldehyde, catalysed by a rhodium or cobalt catalyst. The process is equivalent to the formal addition of the H-C bond of formaldehyde across the double bond of an alkene. rsc:db The reverse of a [4+2] cycloaddition reaction, in which an unsaturated six-membered ring compound fragments to give a diene and a compound containing a double or triple bond (a dienophile). retro Diels-Alder reaction RXNO RXNO:0000273 retro-Diels-Alder reaction RXNO:0000273 The reverse of a [4+2] cycloaddition reaction, in which an unsaturated six-membered ring compound fragments to give a diene and a compound containing a double or triple bond (a dienophile). rsc:db The reverse of an aldol addition, in which a beta-hydroxy ketone fragments to form a carbonyl compound and the enolate of an alpha-acidic carbonyl compound. retro-aldol reaction RXNO RXNO:0000274 This process can occur because the whole reaction is an equilibrium. In the forward direction (aldol addition), elimination of water from the beta-hydroxy ketone, giving an alpha,beta-unsaturated ketone, is irreversible, and thus the aldol condensation does not have a "retro" counterpart. retro-aldol addition RXNO:0000274 The reverse of an aldol addition, in which a beta-hydroxy ketone fragments to form a carbonyl compound and the enolate of an alpha-acidic carbonyl compound. rsc:db A hydrogenation in which a metal-ligating group distant from the reacting alkene directs the attack of hydrogen, giving preferentially one stereoisomer of the product. RXNO RXNO:0000275 Stork-Crabtree hydrogenation RXNO:0000275 A hydrogenation in which a metal-ligating group distant from the reacting alkene directs the attack of hydrogen, giving preferentially one stereoisomer of the product. doi:10.1021/jo00364a007 rsc:db The insertion of alkenes (usually ethene) into the Al-C bond of an aluminium alkyl, to give a long-chain aluminium alkyl that can go on to react again, or can decompose into the corresponding terminal alkene. The addition of transition metals results in reliable production of high molecular weight polymers. "Aufbau" reaction 'Aufbau' reaction Aufbau process RXNO RXNO:0000276 Aufbau reaction RXNO:0000276 The insertion of alkenes (usually ethene) into the Al-C bond of an aluminium alkyl, to give a long-chain aluminium alkyl that can go on to react again, or can decompose into the corresponding terminal alkene. The addition of transition metals results in reliable production of high molecular weight polymers. rsc:db The reaction of an aluminium alkyl with an alkene, to give an intermediate aluminium species that can give various products after work-up. RXNO RXNO:0000277 hydroalumination RXNO:0000277 The reaction of an aluminium alkyl with an alkene, to give an intermediate aluminium species that can give various products after work-up. rsc:db The reaction of two alkenes to give an elongated alkene, employing a transition-metal-based catalyst. 1,2-hydrovinylation RXNO RXNO:0000278 hydrovinylation RXNO:0000278 The reaction of two alkenes to give an elongated alkene, employing a transition-metal-based catalyst. rsc:db The reaction of a 1,3-diene with an alkene to give a 1,4-diene, usually employing a cobalt-based catalyst (see Hilt and Luers, Synthesis, 2002, 609). RXNO RXNO:0000279 1,4-hydrovinylation RXNO:0000279 The reaction of a 1,3-diene with an alkene to give a 1,4-diene, usually employing a cobalt-based catalyst (see Hilt and Luers, Synthesis, 2002, 609). rsc:db A joining reaction in which two carbon-carbon double bonds are redistributed among two fragments, i.e. two alkenes. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of a low-MW alkene. Grubbs metathesis Grubbs reaction cross metathesis cross-metathesis olefin metathesis transalkylidenation RXNO RXNO:0000280 alkene metathesis RXNO:0000280 A joining reaction in which two carbon-carbon double bonds are redistributed among two fragments, i.e. two alkenes. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of a low-MW alkene. rsc:db A joining reaction in which two carbon-carbon triple bonds are redistributed among two fragments, i.e. two alkynes. It is catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutenes). The reaction is driven by release of a low-MW alkyne. RXNO RXNO:0000281 alkyne metathesis RXNO:0000281 A joining reaction in which two carbon-carbon triple bonds are redistributed among two fragments, i.e. two alkynes. It is catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutenes). The reaction is driven by release of a low-MW alkyne. rsc:db A joining reaction in which a carbon-carbon double bond and a carbon-carbon triple bond are redistributed among two fragments, i.e. an alkene and an alkyne. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutenes). As a low-MW alkene is not released, the reaction is usually driven by formation of a ring. RXNO RXNO:0000282 enyne metathesis RXNO:0000282 A joining reaction in which a carbon-carbon double bond and a carbon-carbon triple bond are redistributed among two fragments, i.e. an alkene and an alkyne. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutenes). As a low-MW alkene is not released, the reaction is usually driven by formation of a ring. rsc:db A joining reaction in which a carbon-carbon double bond and a carbon-carbon triple bond in the same molecule are redistributed to give a alkene-substituted cycloalkene. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by formation of the ring. ring closing enyne metathesis RXNO RXNO:0000283 ring-closing enyne metathesis RXNO:0000283 A joining reaction in which a carbon-carbon double bond and a carbon-carbon triple bond in the same molecule are redistributed to give a alkene-substituted cycloalkene. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by formation of the ring. rsc:db A ring-breaking reaction in which two carbon-carbon double bonds are redistributed among two fragments, i.e. an alkene and a cycloalkene. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of ring strain in the cycloalkene. ring opening metathesis RXNO RXNO:0000284 ring-opening metathesis RXNO:0000284 A ring-breaking reaction in which two carbon-carbon double bonds are redistributed among two fragments, i.e. an alkene and a cycloalkene. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of ring strain in the cycloalkene. rsc:db A carbon-carbon coupling reaction where an aldehyde or ketone reacts with an allyl halide and zinc to give a homoallylic alcohol. RXNO RXNO:0000285 Not to be confused with the Luche reduction (the chemoselective reduction of an enone to an allylic alcohol). Luche reaction RXNO:0000285 A carbon-carbon coupling reaction where an aldehyde or ketone reacts with an allyl halide and zinc to give a homoallylic alcohol. https://orcid.org/0000-0002-4077-4719 rsc:db The chemoselective reduction of an enone to give an allylic alcohol, using sodium borohydride and an lanthanoid chloride, typically cerium chloride. RXNO RXNO:0000286 Not to be confused with the Luche reaction (the coupling of an aldehyde or ketone with an allyl halide). Luche reduction RXNO:0000286 The chemoselective reduction of an enone to give an allylic alcohol, using sodium borohydride and an lanthanoid chloride, typically cerium chloride. https://orcid.org/0000-0002-4077-4719 rsc:db The oxidation of an aldehyde to a carboxylic acid with chlorite. RXNO RXNO:0000287 Lindgren oxidation RXNO:0000287 The oxidation of an aldehyde to a carboxylic acid with chlorite. doi:10.3891/acta.chem.scand.27-0888 https://orcid.org/0000-0002-4077-4719 rsc:db A carbon-carbon coupling reaction where an aryl halide reacts with copper(I) cyanide to give an aryl nitrile. https://www.rsc.org/Merck-Index/reaction/r376/ Rosenmund-von Braun synthesis RXNO RXNO:0000288 Rosenmund-von Braun reaction RXNO:0000288 A carbon-carbon coupling reaction where an aryl halide reacts with copper(I) cyanide to give an aryl nitrile. https://orcid.org/0000-0002-4077-4719 rsc:db The formation of urea from ammonium cyanate. Ammonium cyanate is unstable, and so is formed in situ from either (a) cyanic acid and ammonia, (b) a metal cyanate and an ammonium salt, or (c) a metal cyanate and ammonia. Woehler synthesis Wohler reaction Wohler synthesis RXNO RXNO:0000289 Woehler reaction RXNO:0000289 The formation of urea from ammonium cyanate. Ammonium cyanate is unstable, and so is formed in situ from either (a) cyanic acid and ammonia, (b) a metal cyanate and an ammonium salt, or (c) a metal cyanate and ammonia. https://orcid.org/0000-0002-4077-4719 rsc:db The addition of a hydrosilane across the double bond of an alkene or alkyne to give a more substituted silane. Addition to an aldehyde or ketone produces a silyl ether. hydrosilation RXNO RXNO:0000290 hydrosilylation RXNO:0000290 The addition of a hydrosilane across the double bond of an alkene or alkyne to give a more substituted silane. Addition to an aldehyde or ketone produces a silyl ether. https://orcid.org/0000-0002-4077-4719 rsc:db The addition of the N-H bond of an amine across a double bond of an alkene or alkyne, to give a more substituted amine. RXNO RXNO:0000291 hydroamination RXNO:0000291 The addition of the N-H bond of an amine across a double bond of an alkene or alkyne, to give a more substituted amine. https://orcid.org/0000-0002-4077-4719 rsc:db The addition of a boron hydride across a double bond of an alkene or alkyne. The boron usually adds to the less substituted carbon. RXNO RXNO:0000292 hydroboration RXNO:0000292 The addition of a boron hydride across a double bond of an alkene or alkyne. The boron usually adds to the less substituted carbon. https://orcid.org/0000-0002-4077-4719 rsc:db The formal addition of water across a double bond of an alkene or alkyne by formation of an organoborane and in situ oxidation, typically with basic peroxide. The product is usually the less substituted alcohol. RXNO RXNO:0000293 hydroboration-oxidation RXNO:0000293 The formal addition of water across a double bond of an alkene or alkyne by formation of an organoborane and in situ oxidation, typically with basic peroxide. The product is usually the less substituted alcohol. https://orcid.org/0000-0002-4077-4719 rsc:db The reaction of any of a number of metal hydride species with an alkene or alkyne, to give an intermediate organometal species that can give various products after work-up. hydrometalation RXNO RXNO:0000294 hydrometallation RXNO:0000294 The reaction of any of a number of metal hydride species with an alkene or alkyne, to give an intermediate organometal species that can give various products after work-up. https://orcid.org/0000-0002-4077-4719 rsc:db The reaction of a organozirconium hydride with an alkene or alkyne, to give an intermediate zirconium species that can give various products after work-up. The zirconium reagent used is typically Schwartz's reagent, Cp2ZrHCl. RXNO RXNO:0000295 hydrozirconation RXNO:0000295 The reaction of a organozirconium hydride with an alkene or alkyne, to give an intermediate zirconium species that can give various products after work-up. The zirconium reagent used is typically Schwartz's reagent, Cp2ZrHCl. https://orcid.org/0000-0002-4077-4719 rsc:db The reaction of a organotin hydride with an alkene or alkyne, to give an intermediate tin species that can give various products after work-up. RXNO RXNO:0000296 hydrostannylation RXNO:0000296 The reaction of a organotin hydride with an alkene or alkyne, to give an intermediate tin species that can give various products after work-up. https://orcid.org/0000-0002-4077-4719 rsc:db The reaction of a organotellurium hydride with an alkyne, to give a (usually (Z)-configured) vinyltellurium species. RXNO RXNO:0000297 hydrotelluration RXNO:0000297 The reaction of a organotellurium hydride with an alkyne, to give a (usually (Z)-configured) vinyltellurium species. https://orcid.org/0000-0002-4077-4719 rsc:db The oxidation of a primary alcohol to an aldehyde or a secondary alcohol to a ketone using Fetizon's reagent. RXNO RXNO:0000298 Fetizon oxidation RXNO:0000298 The oxidation of a primary alcohol to an aldehyde or a secondary alcohol to a ketone using Fetizon's reagent. :cg rsc:db The substitution of an acylated sugar with a silylated base to give a nucleoside. Vorbrueggen glycosylation Vorbruggen condensation Vorbruggen glycosylation RXNO RXNO:0000299 Vorbrueggen condensation RXNO:0000299 The substitution of an acylated sugar with a silylated base to give a nucleoside. : https://orcid.org/0000-0002-4077-4719 rsc:db The addition of a thiol across the double bond of an alkene to give a thioether. thiol-ene click reaction RXNO RXNO:0000300 thiol-ene reaction RXNO:0000300 The addition of a thiol across the double bond of an alkene to give a thioether. :cg rsc:db The nickel-catalysed carbon-carbon coupling of a dihaloaromatic compound or aromatic bistriflate to give a polymer. Yamamoto coupling Yamamoto polymerization RXNO RXNO:0000301 Yamamoto polymerisation RXNO:0000301 The nickel-catalysed carbon-carbon coupling of a dihaloaromatic compound or aromatic bistriflate to give a polymer. https://orcid.org/0000-0002-4077-4719 rsc:db The thermally induced addition of a hydrosilane across the double bond of an alkene or alkyne to give a more substituted silane, usually applied to cases where the hydrosilane is part of a silicon surface. RXNO RXNO:0000302 thermal hydrosilylation RXNO:0000302 The thermally induced addition of a hydrosilane across the double bond of an alkene or alkyne to give a more substituted silane, usually applied to cases where the hydrosilane is part of a silicon surface. :cg rsc:db The photochemically induced addition of a hydrosilane across the double bond of an alkene or alkyne to give a more substituted silane, usually applied to cases where the hydrosilane is part of a silicon surface. The reaction uses UV irradiation and is usually initiated by an added photoactive compound such as a platinum catalyst. photo-hydrosilylation RXNO RXNO:0000303 photohydrosilylation RXNO:0000303 The photochemically induced addition of a hydrosilane across the double bond of an alkene or alkyne to give a more substituted silane, usually applied to cases where the hydrosilane is part of a silicon surface. The reaction uses UV irradiation and is usually initiated by an added photoactive compound such as a platinum catalyst. :cg rsc:db A carbon-carbon coupling reaction between a tetrazole sulfone and an aldehyde or ketone to give a (typically trans) alkene. Julia-Kocienski coupling Julia-Kocienski reaction RXNO RXNO:0000304 Julia-Kocienski olefination RXNO:0000304 A carbon-carbon coupling reaction between a tetrazole sulfone and an aldehyde or ketone to give a (typically trans) alkene. rsc:db The conversion of a selenoxide with an alpha-hydrogen to an alpha-subtituted selenoether. selenoxide Pummerer reaction RXNO RXNO:0000305 seleno-Pummerer rearrangement RXNO:0000305 The conversion of a selenoxide with an alpha-hydrogen to an alpha-subtituted selenoether. rsc:db A carbon-carbon coupling reaction where an organohalide or triflate couples to an alkene in the same molecule, catalysed by palladium. intramolecular Heck-Mizoroki RXNO RXNO:0000306 intramolecular Heck reaction RXNO:0000306 A carbon-carbon coupling reaction where an organohalide or triflate couples to an alkene in the same molecule, catalysed by palladium. rsc:db An intramolecular Heck reaction of an ortho-halo-aniline with an alkene, catalysed by palladium. Mori-Ban indole reaction RXNO RXNO:0000307 Mori-Ban indole synthesis RXNO:0000307 An intramolecular Heck reaction of an ortho-halo-aniline with an alkene, catalysed by palladium. rsc:db The intramolecular esterification of a carboxylic acid group with an alcohol group using 2,4,6-trichlorobenzoyl chloride (Yamaguchi reagent) - an intramolecular Yamaguchi esterification. Yamaguchi lactonization RXNO RXNO:0000308 Yamaguchi lactonisation RXNO:0000308 The intramolecular esterification of a carboxylic acid group with an alcohol group using 2,4,6-trichlorobenzoyl chloride (Yamaguchi reagent) - an intramolecular Yamaguchi esterification. rsc:db The esterification of a carboxylic acid with an alcohol using 2,4,6-trichlorobenzoyl chloride (Yamaguchi reagent). https://www.rsc.org/Merck-Index/reaction/r479/ RXNO RXNO:0000309 Yamaguchi esterification RXNO:0000309 The esterification of a carboxylic acid with an alcohol using 2,4,6-trichlorobenzoyl chloride (Yamaguchi reagent). rsc:db A Diels-Alder reaction between a diene and an aldehyde or ketone to give a six-membered oxygen-containing ring compound. oxa Diels-Alder cycloaddition oxa Diels-Alder reaction oxa-Diels-Alder cycloaddition oxo Diels-Alder cycloaddition oxo Diels-Alder reaction oxo-Diels-Alder cycloaddition oxo-Diels-Alder reaction RXNO RXNO:0000310 oxa-Diels-Alder reaction RXNO:0000310 A Diels-Alder reaction between a diene and an aldehyde or ketone to give a six-membered oxygen-containing ring compound. rsc:db A carbon-carbon coupling reaction in which a nucleophile reacts with an allyl acetate, allyl halide, allyl carbonate, allyl carbamate, allyl phosphate, allyl sulfone or allyl nitro compound to give an allyl compound. The reaction is catalsed by Pd(0). Trost allylation RXNO RXNO:0000311 Tsuji-Trost reaction RXNO:0000311 A carbon-carbon coupling reaction in which a nucleophile reacts with an allyl acetate, allyl halide, allyl carbonate, allyl carbamate, allyl phosphate, allyl sulfone or allyl nitro compound to give an allyl compound. The reaction is catalsed by Pd(0). rsc:db A ring rearrangement reaction where an amine reacts with a 2,5-dialkoxytetrahydrofuran to give a pyrrole. Clauson-Kaas pyrrole synthesis RXNO RXNO:0000312 Clauson-Kaas reaction RXNO:0000312 A ring rearrangement reaction where an amine reacts with a 2,5-dialkoxytetrahydrofuran to give a pyrrole. http://www.clauson-kaas.com/cgi-files/mdmgfx/file-709-116554-7465.pdf A [4+2] cycloaddition reaction where a diene (or heterocyclic analogue) reacts with a dienophile to form an unsaturated heterocyclic six-membered ring compound. RXNO RXNO:0000313 hetero-Diels-Alder reaction RXNO:0000313 A [4+2] cycloaddition reaction where a diene (or heterocyclic analogue) reacts with a dienophile to form an unsaturated heterocyclic six-membered ring compound. rsc:djb true RXNO:0000314 true RXNO:0000315 A carbon-carbon coupling reaction that is catalysed by a palladium atom. RXNO RXNO:0000316 palladium-catalysed carbon-carbon coupling reaction RXNO:0000316 A carbon-carbon coupling reaction that is catalysed by a palladium atom. https://orcid.org/0000-0001-5985-7429 A condensation reaction that results in the production of an ester. NAMERXN:3.6 RXNO RXNO:0000317 ester condensation reaction RXNO:0000317 A condensation reaction that results in the production of an ester. https://orcid.org/0000-0001-5985-7429 true RXNO:0000318 true RXNO:0000319 A deprotection reaction where the reactive centre is an amino nitrogen atom. RXNO RXNO:0000320 amino group deprotection RXNO:0000320 A deprotection reaction where the reactive centre is an amino nitrogen atom. https://orcid.org/0000-0001-5985-7429 A protection reaction where the reactive centre is an amino nitrogen atom. RXNO RXNO:0000321 amino group protection RXNO:0000321 A protection reaction where the reactive centre is an amino nitrogen atom. https://orcid.org/0000-0001-5985-7429 An amino group protection where the amino nitrogen atom is protected by reaction with benzylamine. RXNO RXNO:0000322 benzylamine protection RXNO:0000322 An amino group protection where the amino nitrogen atom is protected by reaction with benzylamine. https://orcid.org/0000-0001-5985-7429 A protection reaction where the reactive centre is a hydroxyl oxygen atom. RXNO RXNO:0000323 hydroxyl group protection RXNO:0000323 A protection reaction where the reactive centre is a hydroxyl oxygen atom. https://orcid.org/0000-0001-5985-7429 A hydroxyl group protection where the hydroxyl oxygen atom is protected by formation of a benzyl ether. RXNO RXNO:0000324 benzyl ether protection RXNO:0000324 A hydroxyl group protection where the hydroxyl oxygen atom is protected by formation of a benzyl ether. https://orcid.org/0000-0001-5985-7429 A protection reaction where the reactive centre is a carboxy oxygen. RXNO RXNO:0000325 carboxylic acid protection RXNO:0000325 A protection reaction where the reactive centre is a carboxy oxygen. https://orcid.org/0000-0001-5985-7429 An amino group deprotection reaction where a tertbutoxycarbonyl group is removed in acid conditions. RXNO RXNO:0000326 Boc deprotection RXNO:0000326 An amino group deprotection reaction where a tertbutoxycarbonyl group is removed in acid conditions. https://orcid.org/0000-0001-5985-7429 An amino group deprotection reaction where a benzylamine group is removed by hydrogenation. RXNO RXNO:0000327 benzylamine deprotection RXNO:0000327 An amino group deprotection reaction where a benzylamine group is removed by hydrogenation. https://orcid.org/0000-0001-5985-7429 A hydroxyl group protection where the hydroxyl oxygen atom is protected by formation of a silyl ether. RXNO RXNO:0000328 silyl protection RXNO:0000328 A hydroxyl group protection where the hydroxyl oxygen atom is protected by formation of a silyl ether. https://orcid.org/0000-0001-5985-7429 An experimental procedure with the aim of producing a portion of a given compound or mixture. RXNO RXNO:0000329 planned synthesis RXNO:0000329 An experimental procedure with the aim of producing a portion of a given compound or mixture. https://orcid.org/0000-0001-5985-7429 A hydroxyl group protection where the hydroxyl oxygen atom is protected by formation of an acetate ester. O-Ac protection RXNO RXNO:0000330 acetate protection RXNO:0000330 A hydroxyl group protection where the hydroxyl oxygen atom is protected by formation of an acetate ester. https://orcid.org/0000-0001-5985-7429 A functional modification step in which one singly-bonded substituent, but not a hydrogen, is replaced by another singly-bonded substituent. RXNO RXNO:0000331 substitution step RXNO:0000331 A functional modification step in which one singly-bonded substituent, but not a hydrogen, is replaced by another singly-bonded substituent. https://orcid.org/0000-0001-5985-7429 A substitution step where one singly-bonded substituent on an aromatic skeleton is replaced by another singly-bonded substituent. RXNO RXNO:0000332 aromatic substitution step RXNO:0000332 A substitution step where one singly-bonded substituent on an aromatic skeleton is replaced by another singly-bonded substituent. https://orcid.org/0000-0001-5985-7429 An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) halide to form an aromatic halide. RXNO RXNO:0000333 Sandmeyer halogenation RXNO:0000333 An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) halide to form an aromatic halide. RSC:db An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(II) pseudohalide to form an aromatic pseudohalide. RXNO RXNO:0000334 Sandmeyer pseudohalogenation RXNO:0000334 An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(II) pseudohalide to form an aromatic pseudohalide. RSC:db A functional group modification where a carbonyl oxygen is replaced by an amine. batchelorc 2012-03-22T12:15:29Z NAMERXN:1.2 RXNO RXNO:0000335 reductive amination RXNO:0000335 A functional group modification where a carbonyl oxygen is replaced by an amine. https://orcid.org/0000-0001-5985-7429 true RXNO:0000336 A reduction reaction where a nitro group is reduced to an amino group. batchelorc 2012-03-22T12:28:47Z NAMERXN:7.1 RXNO RXNO:0000337 nitro reduction to amine RXNO:0000337 A reduction reaction where a nitro group is reduced to an amino group. https://orcid.org/0000-0001-5985-7429 A reduction process where an amide is transformed into an amine. batchelorc 2012-03-22T12:29:51Z NAMERXN:7.2 RXNO RXNO:0000338 amide reduction to amine RXNO:0000338 A reduction process where an amide is transformed into an amine. https://orcid.org/0000-0001-5985-7429 A hydrogenation reaction where an alkene is reduced to an alkane. batchelorc 2012-03-22T12:30:40Z NAMERXN:7.6 RXNO RXNO:0000339 alkene reduction to alkane RXNO:0000339 A hydrogenation reaction where an alkene is reduced to an alkane. https://orcid.org/0000-0001-5985-7429 An N-alkylation where the reactive centre is an amide nitrogen. batchelorc 2012-03-22T03:07:17Z NAMERXN:1.4 RXNO RXNO:0000340 amide N-alkylation RXNO:0000340 An N-alkylation where the reactive centre is an amide nitrogen. https://orcid.org/0000-0001-5985-7429 An N-alkylation where the reactive centre is an aniline nitrogen. batchelorc 2012-03-22T03:07:44Z NAMERXN:1.5 RXNO RXNO:0000341 aniline N-alkylation RXNO:0000341 An N-alkylation where the reactive centre is an aniline nitrogen. https://orcid.org/0000-0001-5985-7429 A reduction where a nitrile is replaced by an amine function. batchelorc 2012-03-22T03:12:31Z RXNO RXNO:0000342 nitrile reduction to amine RXNO:0000342 A reduction where a nitrile is replaced by an amine function. https://orcid.org/0000-0001-5985-7429 A reduction reaction where an imine function is replaced by an amine. batchelorc 2012-03-22T03:13:12Z RXNO RXNO:0000343 imine reduction to amine RXNO:0000343 A reduction reaction where an imine function is replaced by an amine. https://orcid.org/0000-0001-5985-7429 An alkene oxidation where the carbon-carbon double bond is cleaved. batchelorc 2012-03-22T03:15:25Z NAMERXN:1.6 RXNO RXNO:0000344 alkene oxidative cleavage RXNO:0000344 An alkene oxidation where the carbon-carbon double bond is cleaved. https://orcid.org/0000-0001-5985-7429 An N-alkylation reaction where the reactive centre is an azacycle ring nitrogen. batchelorc 2012-03-22T03:22:27Z NAMERXN:1.1 RXNO RXNO:0000345 heteroaryl N-alkylation RXNO:0000345 An N-alkylation reaction where the reactive centre is an azacycle ring nitrogen. https://orcid.org/0000-0001-5985-7429 A ring formation reaction where the intended product contains an oxacycle that was not in any of the reactants. batchelorc 2012-03-22T03:24:06Z NAMERXN:4.2 RXNO RXNO:0000346 oxacycle synthesis RXNO:0000346 A ring formation reaction where the intended product contains an oxacycle that was not in any of the reactants. https://orcid.org/0000-0001-5985-7429 A ring formation reaction where the intended product contains an azacycle that was not in any of the reactants. batchelorc 2012-03-22T03:24:12Z NAMERXN:4.1 RXNO RXNO:0000347 azacycle synthesis RXNO:0000347 A ring formation reaction where the intended product contains an azacycle that was not in any of the reactants. https://orcid.org/0000-0001-5985-7429 A ring formation reaction where the intended product contains an thiacycle that was not in any of the reactants. batchelorc 2012-03-22T03:24:23Z NAMERXN:4.3 RXNO RXNO:0000348 thiacycle synthesis RXNO:0000348 A ring formation reaction where the intended product contains an thiacycle that was not in any of the reactants. https://orcid.org/0000-0001-5985-7429 A ring formation reaction where the intended product contains a heterocycle that was not in any of the reactants. batchelorc 2012-03-22T03:24:34Z NAMERXN:4 RXNO RXNO:0000349 heterocycle synthesis RXNO:0000349 A ring formation reaction where the intended product contains a heterocycle that was not in any of the reactants. https://orcid.org/0000-0001-5985-7429 A hydrogenation reaction where an alkyne is reduced to an alkane. batchelorc 2012-03-22T03:30:01Z NAMERXN:7.7 RXNO RXNO:0000350 alkyne reduction to alkane RXNO:0000350 A hydrogenation reaction where an alkyne is reduced to an alkane. https://orcid.org/0000-0001-5985-7429 A hydrogenation reaction where an aryl ring is reduced to a cycloalkyl ring. batchelorc 2012-03-22T03:30:50Z RXNO RXNO:0000351 aryl reduction to cycloalkyl RXNO:0000351 A hydrogenation reaction where an aryl ring is reduced to a cycloalkyl ring. https://orcid.org/0000-0001-5985-7429 A hydrogenation reaction where a heteroaryl is reduced to a saturated heterocycle. batchelorc 2012-03-22T03:31:49Z RXNO RXNO:0000352 heteroaryl reduction to saturated heterocycle RXNO:0000352 A hydrogenation reaction where a heteroaryl is reduced to a saturated heterocycle. https://orcid.org/0000-0001-5985-7429 An alcohol oxidation where the alcohol centre is replaced with a carboxy group. batchelorc 2012-03-22T03:34:20Z RXNO RXNO:0000353 alcohol oxidation to carboxylic acid RXNO:0000353 An alcohol oxidation where the alcohol centre is replaced with a carboxy group. https://orcid.org/0000-0001-5985-7429 An oxidation reaction where a carbon centre bonded to the benzene ring is oxidized to a carboxyl group. batchelorc 2012-03-22T03:37:52Z RXNO RXNO:0000354 benzylic oxidation RXNO:0000354 An oxidation reaction where a carbon centre bonded to the benzene ring is oxidized to a carboxyl group. https://orcid.org/0000-0001-5985-7429 An oxidation reaction where an allylic C-H bond is replaced by a C=O bond. batchelorc 2012-03-22T03:39:47Z RXNO RXNO:0000355 This can be done with, for instance, selenium dioxide. allylic oxidation RXNO:0000355 An oxidation reaction where an allylic C-H bond is replaced by a C=O bond. http://www.chemtube3d.com/ox_se_allylic.html https://orcid.org/0000-0001-5985-7429 An oxidation reaction where an alcohol is oxidized to the corresponding carbonyl compound by a dichromate ion. batchelorc 2012-03-22T03:39:47Z RXNO RXNO:0000356 Jones oxidation RXNO:0000356 An oxidation reaction where an alcohol is oxidized to the corresponding carbonyl compound by a dichromate ion. http://www.chemtube3d.com/ox_jones_oxidation.html https://orcid.org/0000-0001-5985-7429 An acylation reaction where a nitrogen atom is acylated to form an amide. batchelorc 2012-03-22T03:39:47Z NAMERXN:2.1 RXNO RXNO:0000357 N-acylation to amide RXNO:0000357 An acylation reaction where a nitrogen atom is acylated to form an amide. https://orcid.org/0000-0001-5985-7429 An acylation reaction where a nitrogen atom is acylated to form a urea. batchelorc 2012-03-22T03:39:47Z NAMERXN:2.3 RXNO RXNO:0000358 N-acylation to urea RXNO:0000358 An acylation reaction where a nitrogen atom is acylated to form a urea. https://orcid.org/0000-0001-5985-7429 An N-acylation reaction where a nitrogen centre is acylated to form a carbamate. batchelorc 2012-03-22T04:09:47Z NAMERXN:2.4 RXNO RXNO:0000359 N-acylation to carbamate RXNO:0000359 An N-acylation reaction where a nitrogen centre is acylated to form a carbamate. https://orcid.org/0000-0001-5985-7429 An O-acylation reaction where an oxygen centre is acylated to result in an ester. batchelorc 2012-03-22T04:10:47Z NAMERXN:2.6 RXNO RXNO:0000360 O-acylation to ester RXNO:0000360 An O-acylation reaction where an oxygen centre is acylated to result in an ester. https://orcid.org/0000-0001-5985-7429 A functional group modification where a nitrile reacts with an alcohol under acid catalysis to form an amidine or ester. RXNO RXNO:0000361 Pinner reaction RXNO:0000361 A functional group modification where a nitrile reacts with an alcohol under acid catalysis to form an amidine or ester. https://orcid.org/0000-0001-5985-7429 An oxidation reaction where a nitrile reacts with an alcohol to form an alkyl imidate. RXNO RXNO:0000362 nitrile alcoholysis RXNO:0000362 An oxidation reaction where a nitrile reacts with an alcohol to form an alkyl imidate. https://orcid.org/0000-0001-5985-7429 A functional group modification where an amide is converted to an imidoyl chloride. batchelorc 2012-03-22T05:04:20Z NAMERXN:9.2 RXNO RXNO:0000363 amide to imidoyl chloride conversion RXNO:0000363 A functional group modification where an amide is converted to an imidoyl chloride. https://orcid.org/0000-0001-5985-7429 A functional group modification where an alcohol is converted to a halide. batchelorc 2012-03-22T05:05:15Z NAMERXN:9.1 RXNO RXNO:0000364 alcohol to halide conversion RXNO:0000364 A functional group modification where an alcohol is converted to a halide. https://orcid.org/0000-0001-5985-7429 A functional group modification where a carboxylic acid is converted to an acid chloride. batchelorc 2012-03-22T05:06:09Z NAMERXN:9.3 RXNO RXNO:0000365 carboxylic acid to acid chloride conversion RXNO:0000365 A functional group modification where a carboxylic acid is converted to an acid chloride. https://orcid.org/0000-0001-5985-7429 A functional group modification where a nitrile is transformed into a carboxylic acid. batchelorc 2012-03-22T05:12:32Z NAMERXN:9.4 RXNO RXNO:0000366 nitrile to acid conversion RXNO:0000366 A functional group modification where a nitrile is transformed into a carboxylic acid. https://orcid.org/0000-0001-5985-7429 A functional group modification where a carbonyl compound is converted to an imine. batchelorc 2012-03-22T05:17:03Z NAMERXN:9.6 RXNO RXNO:0000367 carbonyl compound to imine conversion RXNO:0000367 A functional group modification where a carbonyl compound is converted to an imine. https://orcid.org/0000-0001-5985-7429 Oxidation of an alkene to an allene by heating with formaldehyde, an amine and an inorganic salt. batchelorc 2014-01-08T13:48:00Z Crabbe homologation RXNO RXNO:0000368 Crabbé homologation RXNO:0000368 Oxidation of an alkene to an allene by heating with formaldehyde, an amine and an inorganic salt. doi:10.1039/c39790000859 https://orcid.org/0000-0001-5985-7429 A carbon-carbon coupling reaction between an arene and a carbonyl compound (an acylation) or an alkyl compound that can form a carbocation (an alkylation) to form a substituted arene. NAMERXN:3.10 RXNO RXNO:0000369 Friedel-Crafts reaction RXNO:0000369 A carbon-carbon coupling reaction between an arene and a carbonyl compound (an acylation) or an alkyl compound that can form a carbocation (an alkylation) to form a substituted arene. https://orcid.org/0000-0001-5985-7429 A functional group modification of a nitrile to a 1H-tetrazole by addition of sodium azide. RXNO RXNO:0000370 Demko-Sharpless reaction RXNO:0000370 A functional group modification of a nitrile to a 1H-tetrazole by addition of sodium azide. doi:10.1021/jo010635w https://orcid.org/0000-0001-5985-7429 A diazotisation that proceeds by the addition of nitrous acid, nitric acid and water, resulting in a diazonium nitrate salt. https://www.rsc.org/Merck-Index/reaction/r174/ RXNO RXNO:0000371 Griess reaction RXNO:0000371 A diazotisation that proceeds by the addition of nitrous acid, nitric acid and water, resulting in a diazonium nitrate salt. https://orcid.org/0000-0001-5985-7429 An N-arylation reaction where the reactive centre is an azacycle ring nitrogen. NAMERXN:1.3 RXNO RXNO:0000372 heteroaryl N-arylation RXNO:0000372 An N-arylation reaction where the reactive centre is an azacycle ring nitrogen. https://orcid.org/0000-0001-5985-7429 A planned reaction step in which a covalent bond is formed between the molecular skeleton and a functional group and where the skeletal bond order is unchanged. NAMERXN:10 RXNO RXNO:0000373 this is not part of David's grand diagram - well spotted Roger functional group addition step RXNO:0000373 A planned reaction step in which a covalent bond is formed between the molecular skeleton and a functional group and where the skeletal bond order is unchanged. https://orcid.org/0000-0001-5985-7429 Arylation of an amine or an alcohol with an arylboronic acid, stannane or siloxane in air with a copper acetate catalyst. Chan-Lam reaction Chan-Lam-Evans coupling Chan-Lam-Evans reaction RXNO RXNO:0000374 The canonical variant is the N-arylation of an amine with an arylboronic acid. Chan-Lam coupling RXNO:0000374 Arylation of an amine or an alcohol with an arylboronic acid, stannane or siloxane in air with a copper acetate catalyst. doi:10.1016/j.tet.2012.06.015 true RXNO:0000375 N-methylation of a primary or secondary amine with formic acid and formaldehyde to yield a tertiary amine. Eschweiler-Clarke reaction RXNO RXNO:0000376 Eschweiler-Clarke methylation RXNO:0000376 N-methylation of a primary or secondary amine with formic acid and formaldehyde to yield a tertiary amine. https://orcid.org/0000-0001-5985-7429 Coupling of two aromatic rings in the presence of a Lewis acid catalyst. https://www.rsc.org/Merck-Index/reaction/r390/ RXNO RXNO:0000377 Scholl reaction RXNO:0000377 Coupling of two aromatic rings in the presence of a Lewis acid catalyst. https://orcid.org/0000-0001-5985-7429 Scholl reaction within a single molecule to form a larger ring system. RXNO RXNO:0000378 intramolecular Scholl reaction RXNO:0000378 Scholl reaction within a single molecule to form a larger ring system. https://orcid.org/0000-0001-5985-7429 Scholl reaction between two aromatic molecules to form a single molecule. RXNO RXNO:0000379 intermolecular Scholl reaction RXNO:0000379 Scholl reaction between two aromatic molecules to form a single molecule. https://orcid.org/0000-0001-5985-7429 Reaction of a cyclohexanone with methyl vinyl ketone to form a fused-ring cyclohexenone. It is a Michael reaction followed by an intramolecular aldol condensation. https://www.rsc.org/Merck-Index/reaction/r373/ RXNO RXNO:0000380 Robinson annulation RXNO:0000380 Reaction of a cyclohexanone with methyl vinyl ketone to form a fused-ring cyclohexenone. It is a Michael reaction followed by an intramolecular aldol condensation. https://orcid.org/0000-0001-5985-7429 Rearrangement of a beta-amino alcohol to yield a carbonyl compound. In the first step the amine is diazotised by reaction with nitrous acid. https://www.rsc.org/Merck-Index/reaction/r432/ RXNO RXNO:0000381 Tiffeneau-Demjanov rearrangement RXNO:0000381 Rearrangement of a beta-amino alcohol to yield a carbonyl compound. In the first step the amine is diazotised by reaction with nitrous acid. https://orcid.org/0000-0001-5985-7429 Substitution reaction of a primary amine via deazotisation to yield a mixture of the corresponding primary alcohol and secondary alcohol. https://www.rsc.org/Merck-Index/reaction/r106/ RXNO RXNO:0000382 TODO: Not *entirely* sure how we classify this. Have given it multiple parentage for the now. Demjanov rearrangement RXNO:0000382 Substitution reaction of a primary amine via deazotisation to yield a mixture of the corresponding primary alcohol and secondary alcohol. https://orcid.org/0000-0001-5985-7429 Reaction of an thiol with an alkyne to form an alkenyl sulfide. 2021-05-05T09:08:42Z alkyne hydrothiolation RXNO RXNO:0000383 thiol-yne reaction RXNO:0000383 Reaction of an thiol with an alkyne to form an alkenyl sulfide. https://en.wikipedia.org/wiki/Thiol-yne_reaction Base-catalysed rearrangement of a cyclic alpha-haloketone to the ring-contracted cyclic carboxylic acid. RXNO RXNO:0000384 cyclic alpha-haloketone Favorskii rearrangement RXNO:0000384 Base-catalysed rearrangement of a cyclic alpha-haloketone to the ring-contracted cyclic carboxylic acid. https://orcid.org/0000-0001-5985-7429 Base-catalysed rearrangement of an alpha-haloketone to a carboxylic acid or ester or amide. RXNO RXNO:0000385 Favorskii rearrangement RXNO:0000385 Base-catalysed rearrangement of an alpha-haloketone to a carboxylic acid or ester or amide. https://orcid.org/0000-0001-5985-7429 Favorskii rearrangement of a cyclic alpha-dibromoketone followed by decarboxylation to yield a ring-contracted cyclic ketone. RXNO RXNO:0000386 Wallach degradation RXNO:0000386 Favorskii rearrangement of a cyclic alpha-dibromoketone followed by decarboxylation to yield a ring-contracted cyclic ketone. https://orcid.org/0000-0001-5985-7429 Reaction of a carbonyl compound with a dimethyl diazomethyl phosphonate under basic conditions to yield an alkyne. https://www.rsc.org/Merck-Index/reaction/r395/ RXNO RXNO:0000387 Seyferth-Gilbert homologation RXNO:0000387 Reaction of a carbonyl compound with a dimethyl diazomethyl phosphonate under basic conditions to yield an alkyne. https://orcid.org/0000-0001-5985-7429 Reaction of an aldehyde with a dimethyl diazomethyl phosphonate under basic conditions to yield a terminal alkyne. RXNO RXNO:0000388 Seyferth-Gilbert aldehyde homologation RXNO:0000388 Reaction of an aldehyde with a dimethyl diazomethyl phosphonate under basic conditions to yield a terminal alkyne. https://orcid.org/0000-0001-5985-7429 Reaction of a ketone with a dimethyl diazomethyl phosphonate under basic conditions to yield a terminal alkyne. RXNO RXNO:0000389 Seyferth-Gilbert ketone homologation RXNO:0000389 Reaction of a ketone with a dimethyl diazomethyl phosphonate under basic conditions to yield a terminal alkyne. https://orcid.org/0000-0001-5985-7429 Seyferth-Gilbert aldehyde homologation where the Seyferth-Gilbert reagent is generated in situ by reaction with methanol and potassium carbonate. https://www.rsc.org/Merck-Index/reaction/r395/ Bestmann modification Ohira-Bestmann homologation Ohira-Bestmann modification RXNO RXNO:0000390 Seyferth-Gilbert-Bestmann homologation RXNO:0000390 Seyferth-Gilbert aldehyde homologation where the Seyferth-Gilbert reagent is generated in situ by reaction with methanol and potassium carbonate. https://orcid.org/0000-0001-5985-7429 Synthesis of a pyrazole by condensation of a 1,3-dicarbonyl compound with a hydrazine, hydrazide, semicarbazide or aminoguanidine. https://www.rsc.org/Merck-Index/reaction/r233/ RXNO RXNO:0000391 Knorr pyrazole synthesis RXNO:0000391 Synthesis of a pyrazole by condensation of a 1,3-dicarbonyl compound with a hydrazine, hydrazide, semicarbazide or aminoguanidine. https://orcid.org/0000-0001-5985-7429 A reaction in which the intended product is a pyrazole that was not present in any of the reactants. RXNO RXNO:0000392 pyrazole synthesis RXNO:0000392 A reaction in which the intended product is a pyrazole that was not present in any of the reactants. https://orcid.org/0000-0001-5985-7429 A reaction in which the intended product is a quinoline that was not present in any of the reactants. RXNO RXNO:0000393 quinoline synthesis RXNO:0000393 A reaction in which the intended product is a quinoline that was not present in any of the reactants. https://orcid.org/0000-0001-5985-7429 Synthesis of an alpha-hydroxyquinoline by reaction of a beta-ketoester and an arylamine then dehydration with concentrated sulfuric acid. https://www.rsc.org/Merck-Index/reaction/r234/ RXNO RXNO:0000394 Knorr quinoline synthesis RXNO:0000394 Synthesis of an alpha-hydroxyquinoline by reaction of a beta-ketoester and an arylamine then dehydration with concentrated sulfuric acid. https://orcid.org/0000-0001-5985-7429 A reaction in which the intended product is an indole that was not present in any of the reactants. RXNO RXNO:0000395 indole synthesis RXNO:0000395 A reaction in which the intended product is an indole that was not present in any of the reactants. https://orcid.org/0000-0001-5985-7429 Palladium-catalysed synthesis of a 2,3-substituted indole by reaction of an ortho-iodoaniline with an internal alkyne. https://www.rsc.org/Merck-Index/reaction/r250/ Larock indolisation Larock indolization RXNO RXNO:0000396 Larock indole synthesis RXNO:0000396 Palladium-catalysed synthesis of a 2,3-substituted indole by reaction of an ortho-iodoaniline with an internal alkyne. https://orcid.org/0000-0001-5985-7429 Reaction of an organic diazo compound with an acetylene to yield a pyrazole. https://www.rsc.org/Merck-Index/reaction/r323/ RXNO RXNO:0000397 Pechmann pyrazole synthesis RXNO:0000397 Reaction of an organic diazo compound with an acetylene to yield a pyrazole. https://orcid.org/0000-0001-5985-7429 A reaction in which the intended product is a benzimidazole that was not present in any of the reactants. RXNO RXNO:0000398 benzimidazole synthesis RXNO:0000398 A reaction in which the intended product is a benzimidazole that was not present in any of the reactants. https://orcid.org/0000-0001-5985-7429 Reaction of an ortho-diaminobenzene with a carboxylic acid under heat to yield a benzimidazole. Phillips benzimidazole condensation RXNO RXNO:0000399 This may be done in the presence of an acid, hexamethyldisilazane in the presence of catalytic triflic acid, a titanium catalyst, elevated pressure, or under UV. [ISBN:9780080534459] Phillips benzimidazole synthesis RXNO:0000399 Reaction of an ortho-diaminobenzene with a carboxylic acid under heat to yield a benzimidazole. ISBN:9780080534459 https://orcid.org/0000-0001-5985-7429 A reaction in which the intended product is a pyrimidine that was not present in any of the reactants. RXNO RXNO:0000400 pyrimidine synthesis RXNO:0000400 A reaction in which the intended product is a pyrimidine that was not present in any of the reactants. https://orcid.org/0000-0001-5985-7429 A reaction in which the intended product is a triazine that was not present in any of the reactants. RXNO RXNO:0000401 triazine synthesis RXNO:0000401 A reaction in which the intended product is a triazine that was not present in any of the reactants. https://orcid.org/0000-0001-5985-7429 Reaction of a 1,3-dicarbonyl compound with an amidine to yield a pyrimidine. RXNO RXNO:0000402 Pinner pyrimidine synthesis RXNO:0000402 Reaction of a 1,3-dicarbonyl compound with an amidine to yield a pyrimidine. https://orcid.org/0000-0001-5985-7429 Reaction of aryl amidines or halogenated aliphatics amidines with phosgene to yield a 2-hydroxy-4,6-diaryl-s-triazine with loss of ammonia. https://www.rsc.org/Merck-Index/reaction/r343/ RXNO RXNO:0000403 Pinner triazine synthesis RXNO:0000403 Reaction of aryl amidines or halogenated aliphatics amidines with phosgene to yield a 2-hydroxy-4,6-diaryl-s-triazine with loss of ammonia. https://orcid.org/0000-0001-5985-7429 Cyclisation-condensation of a beta-arylethanol with an aldehyde to yield an ortho,peri-fused aryl-oxacycle. RXNO RXNO:0000404 oxa-Pictet-Spengler reaction RXNO:0000404 Cyclisation-condensation of a beta-arylethanol with an aldehyde to yield an ortho,peri-fused aryl-oxacycle. https://orcid.org/0000-0001-5985-7429 Epoxidation of an alkene by reaction with a peroxy acid. https://www.rsc.org/Merck-Index/reaction/r351/ Prileschajew reaction Prilezhaev reaction RXNO RXNO:0000405 Prilezhaev epoxidation RXNO:0000405 Epoxidation of an alkene by reaction with a peroxy acid. https://orcid.org/0000-0001-5985-7429 Conversion of an alcohol to an alkyl halide with triphenylphosphine and a halide source. Appel reaction RXNO RXNO:0000406 Appel halogenation RXNO:0000406 Conversion of an alcohol to an alkyl halide with triphenylphosphine and a halide source. doi:10.1002/anie.197508011 https://orcid.org/0000-0001-5985-7429 Conversion of an alcohol to an alkyl iodide with triphenylphosphine and tetraiodomethane. RXNO RXNO:0000407 Appel iodination RXNO:0000407 Conversion of an alcohol to an alkyl iodide with triphenylphosphine and tetraiodomethane. https://orcid.org/0000-0001-5985-7429 Conversion of an alcohol to an alkyl chloride with triphenylphosphine and tetrachloromethane. RXNO RXNO:0000408 Appel chlorination RXNO:0000408 Conversion of an alcohol to an alkyl chloride with triphenylphosphine and tetrachloromethane. https://orcid.org/0000-0001-5985-7429 Conversion of an alcohol to an alkyl bromide with triphenylphosphine and tetrabromomethane or bromine. RXNO RXNO:0000409 Appel bromination RXNO:0000409 Conversion of an alcohol to an alkyl bromide with triphenylphosphine and tetrabromomethane or bromine. https://orcid.org/0000-0001-5985-7429 Rearrangement of a primary carboxylic amide to an isocyanate. RXNO RXNO:0000410 This counts as an end-of-chain chain shortening because the terminal carbon is separated from the skeleton into the isocyanate group. Hofmann rearrangement RXNO:0000410 Rearrangement of a primary carboxylic amide to an isocyanate. https://orcid.org/0000-0001-5985-7429 Conversion of a primary carboxylic amide to the lower homologue primary amine. The first step is the Hofmann rearrangement https://www.rsc.org/Merck-Index/reaction/r209/ RXNO Hofmann degradation RXNO:0000411 Hofmann reaction RXNO:0000411 Conversion of a primary carboxylic amide to the lower homologue primary amine. The first step is the Hofmann rearrangement https://orcid.org/0000-0001-5985-7429 Rearrangement of an O-aryl thiocarbamate to an S-aryl thiocarbamate by migration of the aryl group. https://www.wikidata.org/wiki/Q909753 RXNO RXNO:0000412 Newman-Kwart rearrangement RXNO:0000412 Rearrangement of an O-aryl thiocarbamate to an S-aryl thiocarbamate by migration of the aryl group. https://orcid.org/0000-0001-5985-7429 Substitution of phenol ortho- or para-bromo or iodo groups by a nitro group on treatment with nitrous acid or a nitrite in acetic acid. https://www.rsc.org/Merck-Index/reaction/r484/ https://www.wikidata.org/wiki/Q1061336 RXNO RXNO:0000413 Zincke nitration RXNO:0000413 Substitution of phenol ortho- or para-bromo or iodo groups by a nitro group on treatment with nitrous acid or a nitrite in acetic acid. https://www.rsc.org/Merck-Index/reaction/r484/ A coupling of an aldehyde with an alpha-haloethanoate ester to form the next homologous aldehyde. RXNO RXNO:0000414 These are not necessary-and-sufficient conditions because we can't say "one longer" in OWL. haloethanoate ester-aldehyde Darzens reaction RXNO:0000414 A coupling of an aldehyde with an alpha-haloethanoate ester to form the next homologous aldehyde. https://orcid.org/0000-0001-5985-7429 A coupling of a ketone with an alpha-haloethanoate ester to replace the oxo group with a formyl group. RXNO RXNO:0000415 haloethanoate ester-ketone Darzens reaction RXNO:0000415 A coupling of a ketone with an alpha-haloethanoate ester to replace the oxo group with a formyl group. https://orcid.org/0000-0001-5985-7429 Protection of a primary amino group by reaction with phthalic anhydride. RXNO RXNO:0000418 phthalimide protection RXNO:0000418 Protection of a primary amino group by reaction with phthalic anhydride. https://orcid.org/0000-0001-5985-7429 Conversion of a phthalimide into the corresponding primary amine. RXNO RXNO:0000419 phthalimide deprotection RXNO:0000419 Conversion of a phthalimide into the corresponding primary amine. https://orcid.org/0000-0001-5985-7429 Condensation of a 1,5-diketone with ammonium acetate in acetic acid to form a pyridine. http://dx.doi.org/10.1039/SP543 https://www.wikidata.org/wiki/Q2144364 Krohnke pyridine synthesis RXNO RXNO:0000420 Kröhnke pyridine synthesis RXNO:0000420 Condensation of a 1,5-diketone with ammonium acetate in acetic acid to form a pyridine. https://orcid.org/0000-0001-5985-7429 A Gattermann halogenation where the aryl diazonium salt reacts with copper powder and hydrochloric acid to yield an aromatic chloride. RXNO RXNO:0000421 Gattermann chlorination RXNO:0000421 A Gattermann halogenation where the aryl diazonium salt reacts with copper powder and hydrochloric acid to yield an aromatic chloride. https://orcid.org/0000-0002-4077-4719 A Gattermann halogenation where the aryl diazonium salt reacts with copper powder and hydrobromic acid to yield an aromatic bromide. RXNO RXNO:0000422 Gattermann bromination RXNO:0000422 A Gattermann halogenation where the aryl diazonium salt reacts with copper powder and hydrobromic acid to yield an aromatic bromide. https://orcid.org/0000-0002-4077-4719 A joining reaction between an aldehyde and an alkyl halide or aryl halide or vinyl halide or allyl halide in the presence of metal to give a secondary alcohol. RXNO RXNO:0000426 aldehyde Barbier reaction RXNO:0000426 A joining reaction between an aldehyde and an alkyl halide or aryl halide or vinyl halide or allyl halide in the presence of metal to give a secondary alcohol. RSC:db https://orcid.org/0000-0002-4077-4719 A joining reaction between an ketone and an alkyl halide or aryl halide or vinyl halide or allyl halide in the presence of metal to give a tertiary alcohol. RXNO RXNO:0000427 ketone Barbier reaction RXNO:0000427 A joining reaction between an ketone and an alkyl halide or aryl halide or vinyl halide or allyl halide in the presence of metal to give a tertiary alcohol. RSC:db https://orcid.org/0000-0002-4077-4719 Protection of a hydroxy group by reaction with pivaloyl chloride, resulting in formation of a pivaloyl ester. RXNO RXNO:0000428 pivaloyl protection RXNO:0000428 Protection of a hydroxy group by reaction with pivaloyl chloride, resulting in formation of a pivaloyl ester. https://orcid.org/0000-0001-5985-7429 A hydroxy group deprotection where a pivalate group is removed in acid or base conditions. RXNO RXNO:0000429 pivaloyl deprotection RXNO:0000429 A hydroxy group deprotection where a pivalate group is removed in acid or base conditions. https://orcid.org/0000-0001-5985-7429 A deprotection reaction where the reactive centre is an oxygen atom. alcohol deprotection RXNO RXNO:0000430 hydroxy group deprotection RXNO:0000430 A deprotection reaction where the reactive centre is an oxygen atom. https://orcid.org/0000-0001-5985-7429 A carboxylic acid reduction where the product is the corresponding primary alcohol. RXNO RXNO:0000431 carboxylic acid to primary alcohol reduction RXNO:0000431 A carboxylic acid reduction where the product is the corresponding primary alcohol. https://orcid.org/0000-0001-5985-7429 A carboxy group protection where the product is a tert-butyl ester. RXNO RXNO:0000432 tert-butyl protection RXNO:0000432 A carboxy group protection where the product is a tert-butyl ester. https://orcid.org/0000-0001-5985-7429 A deprotection reaction where the reactive centre is a carboxy oxygen atom. RXNO RXNO:0000433 carboxy group deprotection RXNO:0000433 A deprotection reaction where the reactive centre is a carboxy oxygen atom. https://orcid.org/0000-0001-5985-7429 A deprotection reaction where the reactant is a tert-butyl ester and the product is a carboxylic acid. RXNO RXNO:0000434 tert-butyl ester deprotection RXNO:0000434 A deprotection reaction where the reactant is a tert-butyl ester and the product is a carboxylic acid. https://orcid.org/0000-0001-5985-7429 A deprotection reaction where the reactant is a methyl ester and the product is a carboxylic acid. RXNO RXNO:0000435 methyl ester deprotection RXNO:0000435 A deprotection reaction where the reactant is a methyl ester and the product is a carboxylic acid. https://orcid.org/0000-0001-5985-7429 A deprotection reaction where the reactant is an ethyl ester and the product is a carboxylic acid. RXNO RXNO:0000436 ethyl ester deprotection RXNO:0000436 A deprotection reaction where the reactant is an ethyl ester and the product is a carboxylic acid. https://orcid.org/0000-0001-5985-7429 An objective specification that describes how a molecule's skeleton and substituents are to be transformed by a given experiment. RXNO RXNO:0000437 molecular transformation objective RXNO:0000437 An objective specification that describes how a molecule's skeleton and substituents are to be transformed by a given experiment. https://orcid.org/0000-0001-5985-7429 A molecular transformation specification that specifies that atoms should be lost from the molecular skeleton. RXNO RXNO:0000438 molecular skeleton cleaving objective RXNO:0000438 A molecular transformation specification that specifies that atoms should be lost from the molecular skeleton. RSC:db A molecular transformation specification that specifies that the product should contain a ring that was not in any of the reactants. RXNO RXNO:0000439 molecular ring formation objective RXNO:0000439 A molecular transformation specification that specifies that the product should contain a ring that was not in any of the reactants. RSC:db A molecular transformation specification that specifies that atoms should be added to the molecular skeleton. RXNO RXNO:0000440 molecular skeleton joining objective RXNO:0000440 A molecular transformation specification that specifies that atoms should be added to the molecular skeleton. RSC:db A molecular transformation specification that specifies that the number of rings and number of skeletal atoms should be preserved and that one or more atoms or groups of atoms move from one atom to another. RXNO RXNO:0000441 molecular rearrangement objective RXNO:0000441 A molecular transformation specification that specifies that the number of rings and number of skeletal atoms should be preserved and that one or more atoms or groups of atoms move from one atom to another. RSC:db A molecular transformation specification that specifies that the substituents of a molecule should be changed but the number of atoms in the skeleton and their connectivity, but not necessarily the bond orders, should remain the same. RXNO RXNO:0000442 functional modification objective RXNO:0000442 A molecular transformation specification that specifies that the substituents of a molecule should be changed but the number of atoms in the skeleton and their connectivity, but not necessarily the bond orders, should remain the same. RSC:db Reaction of allyltrimethylsilane with a carbon electrophile to allylate the carbon electrophile. https://www.rsc.org/Merck-Index/reaction/r383/ https://www.wikidata.org/wiki/Q903031 Hosomi-Sakurai reaction RXNO RXNO:0000443 Sakurai reaction RXNO:0000443 Reaction of allyltrimethylsilane with a carbon electrophile to allylate the carbon electrophile. https://orcid.org/0000-0001-5985-7429 Rearrangement of the acyl group in a phenolate ester to the ortho- and/or para-position. It is catalysed by a Lewis acid. https://www.rsc.org/Merck-Index/reaction/r160/ https://www.wikidata.org/wiki/Q574893 photo-Fries rearrangement RXNO RXNO:0000444 Can be promoted by heat or UV. The UV version (photo-Fries) involves a radical mechanism. Fries rearrangement RXNO:0000444 Rearrangement of the acyl group in a phenolate ester to the ortho- and/or para-position. It is catalysed by a Lewis acid. https://orcid.org/0000-0001-5985-7429 Rearrangement of the acyl group in a phenolate ester to the ortho-position. RXNO RXNO:0000445 ortho-Fries rearrangement RXNO:0000445 Rearrangement of the acyl group in a phenolate ester to the ortho-position. https://orcid.org/0000-0001-5985-7429 Rearrangement of the acyl group in a phenolate ester to the para-position. RXNO RXNO:0000446 para-Fries rearrangement RXNO:0000446 Rearrangement of the acyl group in a phenolate ester to the para-position. https://orcid.org/0000-0001-5985-7429 Formylation of a phenol or aromatic amine with hexamethylenetetramine in acidic conditions. https://www.rsc.org/Merck-Index/reaction/r119/ https://www.wikidata.org/wiki/Q903217 RXNO RXNO:0000447 Duff reaction RXNO:0000447 Formylation of a phenol or aromatic amine with hexamethylenetetramine in acidic conditions. https://doi.org/10.1039/JR9450000276 https://doi.org/10.1039/jr9410000547 A molecular skeleton joining adjective that is satisfied by a chain part of a molecular skeleton being lengthened. RXNO RXNO:0000448 molecular chain lengthening objective RXNO:0000448 A molecular skeleton joining adjective that is satisfied by a chain part of a molecular skeleton being lengthened. RSC:xp A molecular skeleton transformation objective that is satisfied by a reaction where the product has fewer rings than the reactants. RXNO RXNO:0000449 molecular ring breaking objective RXNO:0000449 A molecular skeleton transformation objective that is satisfied by a reaction where the product has fewer rings than the reactants. RSC:xp A molecular skeleton transformation objective that is satisfied by a reaction where an existing ring is reduced in size. RXNO RXNO:0000450 molecular ring contraction objective RXNO:0000450 A molecular skeleton transformation objective that is satisfied by a reaction where an existing ring is reduced in size. RSC:xp A carbon-carbon coupling reaction in which an aldehyde reacts with allyltrimethylsilane to form a homoallylic alcohol. RXNO RXNO:0000451 aldehyde Sakurai reaction RXNO:0000451 A carbon-carbon coupling reaction in which an aldehyde reacts with allyltrimethylsilane to form a homoallylic alcohol. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A carbon-carbon coupling reaction in which a ketone reacts with allyltrimethylsilane to form a homoallylic alcohol. RXNO RXNO:0000452 ketone Sakurai reaction RXNO:0000452 A carbon-carbon coupling reaction in which a ketone reacts with allyltrimethylsilane to form a homoallylic alcohol. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A molecular skeleton transformation objective that is satisfied by a reaction in which a functional group undergoes a change that does not affect the number of atoms in (or connectivity of) the skeleton of the molecule. RXNO RXNO:0000453 functional group modification objective RXNO:0000453 A molecular skeleton transformation objective that is satisfied by a reaction in which a functional group undergoes a change that does not affect the number of atoms in (or connectivity of) the skeleton of the molecule. RSC:xp A molecular skeleton transformation objective that is satisfied by a reaction in which a single skeletal atom is removed from the end of a chain. RXNO RXNO:0000454 end-of-chain chain shortening objective RXNO:0000454 A molecular skeleton transformation objective that is satisfied by a reaction in which a single skeletal atom is removed from the end of a chain. RSC:xp A functional group modification objective that is satisfied by a reaction in which a functional group is reduced. RXNO RXNO:0000455 functional reduction objective RXNO:0000455 A functional group modification objective that is satisfied by a reaction in which a functional group is reduced. RSC:xp A functional modification objective that is satisfied by a reaction in which two or more groups of atoms are added to the molecule, resulting in a change of skeletal bond order. RXNO RXNO:0000456 addition objective RXNO:0000456 A functional modification objective that is satisfied by a reaction in which two or more groups of atoms are added to the molecule, resulting in a change of skeletal bond order. RSC:xp A molecular transformation objective that is satisfied by a reaction in which an existing skeletal ring is increased in size. RXNO RXNO:0000457 molecular ring expansion objective RXNO:0000457 A molecular transformation objective that is satisfied by a reaction in which an existing skeletal ring is increased in size. RSC:xp A molecular transformation objective that is satisfied by a reaction in which the number of skeletal rings in a molecule stays the same but the connectivity of the atoms in at least one ring changes. RXNO RXNO:0000458 molecular ring rearrangement objective RXNO:0000458 A molecular transformation objective that is satisfied by a reaction in which the number of skeletal rings in a molecule stays the same but the connectivity of the atoms in at least one ring changes. RSC:xp A carbon-carbon coupling reaction between a beta-ketoester and an alkyl halide to yield an alpha-alkylated ester. https://www.rsc.org/Merck-Index/reaction/r1/ https://www.wikidata.org/wiki/Q1017086 RXNO RXNO:0000459 Subsequent treatment with mild hydrolysis leads to a ketone; concentrated base produces a substituted ester. acetoacetic ester synthesis RXNO:0000459 A carbon-carbon coupling reaction between a beta-ketoester and an alkyl halide to yield an alpha-alkylated ester. https://orcid.org/0000-0001-5985-7429 A reductive coupling reaction between two ester groups in the same molecule to give an acyloin (an alpha-hydroxyketone). RXNO RXNO:0000460 intramolecular acyloin condensation RXNO:0000460 A reductive coupling reaction between two ester groups in the same molecule to give an acyloin (an alpha-hydroxyketone). RSC:db https://orcid.org/0000-0002-4077-4719 A reductive coupling reaction between two ester groups in different molecules to give an acyloin (an alpha-hydroxyketone). RXNO RXNO:0000461 intermolecular acyloin condensation RXNO:0000461 A reductive coupling reaction between two ester groups in different molecules to give an acyloin (an alpha-hydroxyketone). RSC:db https://orcid.org/0000-0002-4077-4719 A molecular transformation objective that is satisfied by a cleaving reaction in which a skeletal atom or group of atoms is removed from the middle of a molecule. RXNO RXNO:0000462 molecular extrusion objective RXNO:0000462 A molecular transformation objective that is satisfied by a cleaving reaction in which a skeletal atom or group of atoms is removed from the middle of a molecule. RSC:xp A molecular transformation objective that is satisfied by a reaction in which the parent molecule breaks up into three or more products. RXNO RXNO:0000463 molecular fragmentation objective RXNO:0000463 A molecular transformation objective that is satisfied by a reaction in which the parent molecule breaks up into three or more products. RSC:xp A [2+2+1] cycloaddition between an alkyne, an alkene and carbon monoxide to form an alpha-beta-unsaturated cyclopentenone. https://www.rsc.org/Merck-Index/reaction/r320/ https://www.wikidata.org/wiki/Q903694 RXNO RXNO:0000464 Pauson-Khand reaction RXNO:0000464 A [2+2+1] cycloaddition between an alkyne, an alkene and carbon monoxide to form an alpha-beta-unsaturated cyclopentenone. doi:10.1039/P19730000975 A molecular transformation objective that is satisfied by a reaction in which a fused ring system is present in a product that was not present in any of the reactants. RXNO RXNO:0000465 fused-ring-system formation objective RXNO:0000465 A molecular transformation objective that is satisfied by a reaction in which a fused ring system is present in a product that was not present in any of the reactants. RSC:xp A molecular transformation objective that is satisfied by a reaction in which a large number of monomers react together to product a polymer consisting of repeating units. RXNO RXNO:0000466 polymerisation objective RXNO:0000466 A molecular transformation objective that is satisfied by a reaction in which a large number of monomers react together to product a polymer consisting of repeating units. RSC:xp A fused-ring-system formation reaction where a flavonol is produced by oxidation of a chalcone with alkaline hydrogen peroxide. https://www.rsc.org/Merck-Index/reaction/r5/ https://www.wikidata.org/wiki/Q903717 RXNO RXNO:0000467 definition source Merck Index Algar-Flynn-Oyamada reaction RXNO:0000467 A fused-ring-system formation reaction where a flavonol is produced by oxidation of a chalcone with alkaline hydrogen peroxide. https://orcid.org/0000-0001-5985-7429 A molecular transformation objective that is satisfied by a reaction in which one singly-bonded substituent, but not a hydrogen, is replaced by another singly-bonded substituent. RXNO RXNO:0000468 molecular substitution objective RXNO:0000468 A molecular transformation objective that is satisfied by a reaction in which one singly-bonded substituent, but not a hydrogen, is replaced by another singly-bonded substituent. RSC:xp Reaction of ortho-hydroxyaryl ketones with aromatic carboxylic acid anhydrides to yield a flavone. RXNO RXNO:0000470 Allan-Robinson flavone synthesis RXNO:0000470 Reaction of ortho-hydroxyaryl ketones with aromatic carboxylic acid anhydrides to yield a flavone. https://orcid.org/0000-0001-5985-7429 Reaction of ortho-hydroxyaryl ketones with aromatic carboxylic acid anhydrides to yield an isoflavone. RXNO RXNO:0000471 Allan-Robinson isoflavone synthesis RXNO:0000471 Reaction of ortho-hydroxyaryl ketones with aromatic carboxylic acid anhydrides to yield an isoflavone. https://orcid.org/0000-0001-5985-7429 Rearrangement of an aldose N-glycoside to a ketose N-glycoside by acid or base catalysis. https://www.rsc.org/Merck-Index/reaction/r8/ https://www.wikidata.org/wiki/Q452196 RXNO RXNO:0000472 definition source Merck Index Amadori rearrangement RXNO:0000472 Rearrangement of an aldose N-glycoside to a ketose N-glycoside by acid or base catalysis. https://orcid.org/0000-0001-5985-7429 Reaction of a ketone with ethoxyacetylene to form an alkoxyethynyl alcohol. https://www.rsc.org/Merck-Index/reaction/r9/ https://www.wikidata.org/wiki/Q16624458 RXNO RXNO:0000473 Arens-van Dorp synthesis RXNO:0000473 Reaction of a ketone with ethoxyacetylene to form an alkoxyethynyl alcohol. https://orcid.org/0000-0001-5985-7429 https://www.rsc.org/Merck-Index/reaction/r9/ Ring expansion of a 2-bromo-2-(alpha-bromobenzyl)-1-benzofuran to a flavonol in alcoholic alkali. https://www.rsc.org/Merck-Index/reaction/r11/ https://www.wikidata.org/wiki/Q3115850 RXNO RXNO:0000474 Auwers synthesis RXNO:0000474 Ring expansion of a 2-bromo-2-(alpha-bromobenzyl)-1-benzofuran to a flavonol in alcoholic alkali. https://orcid.org/0000-0001-5985-7429 https://www.rsc.org/Merck-Index/reaction/r11/ Reaction of ortho-hydroxyaryl ketones with aromatic acid anhydrides to yield a flavone or isoflavone. https://www.rsc.org/Merck-Index/reaction/r6/ https://www.wikidata.org/wiki/Q3046015 RXNO RXNO:0000475 Allan-Robinson reaction RXNO:0000475 Reaction of ortho-hydroxyaryl ketones with aromatic acid anhydrides to yield a flavone or isoflavone. https://orcid.org/0000-0001-5985-7429 https://www.rsc.org/Merck-Index/reaction/r6/ Rearrangement of a propargyl alcohol to an alpha,beta-unsaturated carbonyl compound via an allene intermediate to yield the gamma-substituted product. https://www.rsc.org/Merck-Index/reaction/r278/ https://www.wikidata.org/wiki/Q902668 RXNO RXNO:0000476 Meyer-Schuster rearrangement RXNO:0000476 Rearrangement of a propargyl alcohol to an alpha,beta-unsaturated carbonyl compound via an allene intermediate to yield the gamma-substituted product. https://doi.org/10.1039/b912099h Rearrangement of a propargyl alcohol to an alpha,beta-unsaturated carbonyl compound via an enyne intermediate to yield the beta-substituted product. https://www.rsc.org/Merck-Index/reaction/r278/ RXNO RXNO:0000477 Rupe rearrangement RXNO:0000477 Rearrangement of a propargyl alcohol to an alpha,beta-unsaturated carbonyl compound via an enyne intermediate to yield the beta-substituted product. https://doi.org/10.1039/b912099h A Horner-Wadsworth-Emmons reaction that uses phosphonates with electron-withdrawing groups and dissociating conditions to produce predominantly Z-olefins. Still modification RXNO RXNO:0000478 Still-Gennari modification RXNO:0000478 A Horner-Wadsworth-Emmons reaction that uses phosphonates with electron-withdrawing groups and dissociating conditions to produce predominantly Z-olefins. https://orcid.org/0000-0001-5985-7429 A molecular skeleton joining reaction where the connection formed is a carbon-carbon double bond. RXNO RXNO:0000479 olefination RXNO:0000479 A molecular skeleton joining reaction where the connection formed is a carbon-carbon double bond. https://orcid.org/0000-0001-5985-7429 Reaction of an aldehyde or ketone or carboxylic ester or amide with the Tebbe reagent to yield an olefin or an enol ether or an enamine. https://www.rsc.org/Merck-Index/reaction/r428/ RXNO RXNO:0000480 Tebbe olefination RXNO:0000480 Reaction of an aldehyde or ketone or carboxylic ester or amide with the Tebbe reagent to yield an olefin or an enol ether or an enamine. https://orcid.org/0000-0001-5985-7429 https://www.rsc.org/Merck-Index/reaction/r428/ Cyclization of a enynyl allene to yield a toluene biradical with radical centres on the methyl group and at the meta position. batchelorc 2014-02-28T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r292/ https://www.wikidata.org/wiki/Q89925623 Myers-Saito cyclization Myers-Saito process Myers-Saito reaction RXNO RXNO:0000481 Myers-Saito cyclisation RXNO:0000481 Cyclization of a enynyl allene to yield a toluene biradical with radical centres on the methyl group and at the meta position. https://doi.org/10.1039/b009965l https://orcid.org/0000-0001-5985-7429 Cyclization of a enynyl allene to yield a 1-methyl-5-methylenecyclopenta-1,3-diene biradical with radical centres on the methyl group and methylene group. batchelorc 2014-02-28T09:00:00Z Schmittel cyclization RXNO RXNO:0000482 Schmittel cyclisation RXNO:0000482 Cyclization of a enynyl allene to yield a 1-methyl-5-methylenecyclopenta-1,3-diene biradical with radical centres on the methyl group and methylene group. https://doi.org/10.1039/b009965l https://orcid.org/0000-0001-5985-7429 Copper-catalysed reaction of benzene with a nitrosylating agent and hydrogen peroxide to form an o-nitrosophenol. batchelorc 2014-02-28T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r26/ https://www.wikidata.org/wiki/Q3536586 RXNO RXNO:0000483 Baudisch reaction RXNO:0000483 Copper-catalysed reaction of benzene with a nitrosylating agent and hydrogen peroxide to form an o-nitrosophenol. https://orcid.org/0000-0001-5985-7429 A functional modification objective that is satisfied by deprotecting some functional group. batchelorc 2014-02-28T09:00:00Z RXNO RXNO:0000484 deprotection objective RXNO:0000484 A functional modification objective that is satisfied by deprotecting some functional group. RSC:xp A functional modification objective that is satisfied by protecting some functional group. batchelorc 2014-02-28T09:00:00Z RXNO RXNO:0000485 protection objective RXNO:0000485 A functional modification objective that is satisfied by protecting some functional group. RSC:xp A functional modification objective that is satisfied by a reaction in which two or more groups of atoms are removed from the molecule, resulting in a change of skeletal bond order. batchelorc 2014-02-28T09:00:00Z RXNO RXNO:0000486 molecular skeleton elimination objective RXNO:0000486 A functional modification objective that is satisfied by a reaction in which two or more groups of atoms are removed from the molecule, resulting in a change of skeletal bond order. RSC:xp A molecular skeleton joining objective that is satisfied by a reaction in which one or more atoms are added to the middle of a chain. batchelorc 2014-02-28T09:00:00Z RXNO RXNO:0000487 molecular skeleton insertion objective RXNO:0000487 A molecular skeleton joining objective that is satisfied by a reaction in which one or more atoms are added to the middle of a chain. RSC:xp A molecular skeleton joining objective that is satisfied by a reaction in which one or more atoms are added to the molecular skeleton and a skeletal rearrangement occurs. batchelorc 2014-02-28T09:00:00Z RXNO RXNO:0000488 joining with rearrangement objective RXNO:0000488 A molecular skeleton joining objective that is satisfied by a reaction in which one or more atoms are added to the molecular skeleton and a skeletal rearrangement occurs. RSC:xp A functional modification objective that is satisfied by a reaction in which a covalent bond is formed between the molecular skeleton and a functional group and where the skeletal bond order is unchanged. batchelorc 2014-02-28T09:00:00Z RXNO RXNO:0000489 functional group addition objective RXNO:0000489 A functional modification objective that is satisfied by a reaction in which a covalent bond is formed between the molecular skeleton and a functional group and where the skeletal bond order is unchanged. RSC:xp A functional group modification objective that is satisfied by a reaction in which a functional group is oxidised. batchelorc 2014-02-28T09:00:00Z RXNO RXNO:0000490 functional oxidation objective RXNO:0000490 A functional group modification objective that is satisfied by a reaction in which a functional group is oxidised. RSC:xp Cyclisation of a propargyl alpha,beta-unsaturated ketone where the reactant rearranges to an allenyl vinyl ketone, followed by a Nazarov cyclisation in which a nucleophile 'intercepts' the intermediate carbocation to yield a cyclopentenone substituted at the alpha position opposite the double bond. batchelorc 2014-02-28T12:00:00Z interrupted Nazarov cyclization RXNO RXNO:0000491 interrupted Nazarov cyclisation RXNO:0000491 Cyclisation of a propargyl alpha,beta-unsaturated ketone where the reactant rearranges to an allenyl vinyl ketone, followed by a Nazarov cyclisation in which a nucleophile 'intercepts' the intermediate carbocation to yield a cyclopentenone substituted at the alpha position opposite the double bond. doi:10.1039/c3cs60333d Rearrangement of an N-phenylhydroxamine in acid to yield a para-aminophenol. batchelorc 2014-03-03T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r15/ https://www.wikidata.org/wiki/Q139251 RXNO RXNO:0000492 Bamberger rearrangement RXNO:0000492 Rearrangement of an N-phenylhydroxamine in acid to yield a para-aminophenol. https://orcid.org/0000-0001-5985-7429 https://www.rsc.org/Merck-Index/reaction/r15/ Reaction of an aromatic diazonium compound with an alkali arsenite in the presence of copper or silver to yield an aromatic arsonic acid. batchelorc 2014-03-03T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r19/ RXNO RXNO:0000493 Bart reaction RXNO:0000493 Reaction of an aromatic diazonium compound with an alkali arsenite in the presence of copper or silver to yield an aromatic arsonic acid. https://orcid.org/0000-0001-5985-7429 https://www.rsc.org/Merck-Index/reaction/r19/ Reaction of an ortho-substituted nitroarene with a vinyl Grignard reagent to yield a 7-substituted indole. batchelorc 2014-03-03T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r20/ https://www.wikidata.org/wiki/Q3508929 RXNO RXNO:0000494 Bartoli indole synthesis RXNO:0000494 Reaction of an ortho-substituted nitroarene with a vinyl Grignard reagent to yield a 7-substituted indole. https://orcid.org/0000-0001-5985-7429 Reaction of an aldehyde or ketone with a thioaldehyde or thioketone via a 1,3,4-thiadiazoline intermediate to yield an olefin. batchelorc 2014-03-03T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r23/ Barton olefin synthesis RXNO RXNO:0000495 Barton olefination RXNO:0000495 Reaction of an aldehyde or ketone with a thioaldehyde or thioketone via a 1,3,4-thiadiazoline intermediate to yield an olefin. https://orcid.org/0000-0001-5985-7429 Reaction of a nitroalkene with an alpha-isocyanoacetate to yield a substituted pyrrole. batchelorc 2014-03-03T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r25/ https://www.wikidata.org/wiki/Q4865733 Barton-Zard synthesis RXNO RXNO:0000496 Barton-Zard reaction RXNO:0000496 Reaction of a nitroalkene with an alpha-isocyanoacetate to yield a substituted pyrrole. https://orcid.org/0000-0001-5985-7429 A reaction in which the intended product is a pyrrole that was not present in any of the reactants. batchelorc 2014-03-03T09:00:00Z RXNO RXNO:0000497 pyrrole synthesis RXNO:0000497 A reaction in which the intended product is a pyrrole that was not present in any of the reactants. https://orcid.org/0000-0001-5985-7429 Reduction of an aromatic nitro compound to the corresponding arene by iron in some form in aqueous acid. batchelorc 2014-03-03T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r28/ https://www.wikidata.org/wiki/Q906075 Bechamp reduction RXNO RXNO:0000498 Béchamp reduction RXNO:0000498 Reduction of an aromatic nitro compound to the corresponding arene by iron in some form in aqueous acid. https://orcid.org/0000-0001-5985-7429 Reaction of a benzofurazan 1-oxide with an enamine or enolate to yield a quinoxaline-1,4-dioxide. batchelorc 2014-03-03T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r30/ RXNO RXNO:0000499 definition source Merck Index Beirut reaction RXNO:0000499 Reaction of a benzofurazan 1-oxide with an enamine or enolate to yield a quinoxaline-1,4-dioxide. https://orcid.org/0000-0001-5985-7429 Reaction of a beta-aminovinylketone with a Grignard reagent to yield a substituted alpha,beta-unsaturated carbonyl compound. batchelorc 2014-03-03T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r31/ https://www.wikidata.org/wiki/Q816687 Benary reaction RXNO RXNO:0000500 Bénary reaction RXNO:0000500 Reaction of a beta-aminovinylketone with a Grignard reagent to yield a substituted alpha,beta-unsaturated carbonyl compound. https://orcid.org/0000-0001-5985-7429 Reaction of an alpha-haloketone or alpha-haloether with a 1,3-dicarbonyl compound in the presence of pyridine to yield a substituted furan. batchelorc 2014-03-03T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r138/ https://www.wikidata.org/wiki/Q5441589 RXNO RXNO:0000501 Feist-Bénary synthesis RXNO:0000501 Reaction of an alpha-haloketone or alpha-haloether with a 1,3-dicarbonyl compound in the presence of pyridine to yield a substituted furan. https://orcid.org/0000-0001-5985-7429 Rearrangement of a mancude eight-membered system containing a pentacycle into a different pentacycle where two of the ring atoms are ring atoms in the original molecule. batchelorc 2014-03-04T09:00:00Z https://www.wikidata.org/wiki/Q56298381 RXNO RXNO:0000502 Boulton-Katritzky rearrangement RXNO:0000502 Rearrangement of a mancude eight-membered system containing a pentacycle into a different pentacycle where two of the ring atoms are ring atoms in the original molecule. https://orcid.org/0000-0001-5985-7429 Rearrangement of an azapentacycle containing a -N= system where there is an unsaturated three-heavy-atom substituent XYZ on the substituent double-bonded to the nitrogen, to a new azapentacycle where the pivotal nitrogen has broken its single bond and formed a new bond with atom Z. batchelorc 2014-03-04T09:00:00Z RXNO RXNO:0000503 monocyclic Boulton-Katritzky rearrangement RXNO:0000503 Rearrangement of an azapentacycle containing a -N= system where there is an unsaturated three-heavy-atom substituent XYZ on the substituent double-bonded to the nitrogen, to a new azapentacycle where the pivotal nitrogen has broken its single bond and formed a new bond with atom Z. https://doi.org/10.1039/j39670002005 Rearrangement of a mancude bicyclo[4.3.0] compound with an unsaturated two-heavy-atom substituent on the six-membered ring alpha to the bridgehead to form a new mancude bicyclo[4.3.0] compound where the five-membered ring has been formed from the two-heavy-atom substituent and the original five-membered ring has been broken. batchelorc 2014-03-04T09:00:00Z RXNO RXNO:0000504 bicyclic Boulton-Katritzky rearrangement RXNO:0000504 Rearrangement of a mancude bicyclo[4.3.0] compound with an unsaturated two-heavy-atom substituent on the six-membered ring alpha to the bridgehead to form a new mancude bicyclo[4.3.0] compound where the five-membered ring has been formed from the two-heavy-atom substituent and the original five-membered ring has been broken. https://doi.org/10.1039/j29660001004 Reaction of a primary nitro compound with phenyl isocynatate and triethylamine to yield a nitrile oxide. batchelorc 2014-03-04T09:00:00Z RXNO RXNO:0000505 Mukaiyama-Hoshino method RXNO:0000505 Reaction of a primary nitro compound with phenyl isocynatate and triethylamine to yield a nitrile oxide. https://doi.org/10.1021/ja01505a017 https://orcid.org/0000-0001-5985-7429 Reaction of an aldehyde or ketone with a sodium acetylide to yield a propargyl alcohol. batchelorc 2014-03-04T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r298/ https://www.wikidata.org/wiki/Q16930708 RXNO RXNO:0000506 Nef synthesis RXNO:0000506 Reaction of an aldehyde or ketone with a sodium acetylide to yield a propargyl alcohol. https://orcid.org/0000-0001-5985-7429 Reaction of an ester with an electron-withdrawing group alpha- to the ester functionality with a metal halide or pseudohalide to yield the shorter homologous system. batchelorc 2014-03-04T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r242/ https://www.wikidata.org/wiki/Q4597398 Krapcho decarbalkoxylation RXNO RXNO:0000507 Krapcho decarboxylation RXNO:0000507 Reaction of an ester with an electron-withdrawing group alpha- to the ester functionality with a metal halide or pseudohalide to yield the shorter homologous system. https://orcid.org/0000-0001-5985-7429 Reaction of an aromatic nitro compound with an unsaturated substituent at the alpha-position to form a fused-ring nitrogen heterocycle. batchelorc 2014-03-04T09:00:00Z Cadogan reaction Cadogan ring closure Cadogan ring-closure RXNO RXNO:0000508 Cadogan cyclization RXNO:0000508 Reaction of an aromatic nitro compound with an unsaturated substituent at the alpha-position to form a fused-ring nitrogen heterocycle. https://orcid.org/0000-0001-5985-7429 A Cadogan cyclization that results in an indole. batchelorc 2014-03-05T09:00:00Z RXNO RXNO:0000509 Cadogan indole synthesis RXNO:0000509 A Cadogan cyclization that results in an indole. https://orcid.org/0000-0001-5985-7429 Addition of hydrogen atoms to unsaturated rings by means of alkali metals in low-molecular weight amines. batchelorc 2014-03-06T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r32/ Benkeser reaction RXNO RXNO:0000510 Benkeser reduction RXNO:0000510 Addition of hydrogen atoms to unsaturated rings by means of alkali metals in low-molecular weight amines. https://orcid.org/0000-0001-5985-7429 Reaction of an N-(2-alkylphenyl)alkanamide with strong base to form an indole. batchelorc 2014-03-07T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r261/ https://www.wikidata.org/wiki/Q2632831 Madelung synthesis RXNO RXNO:0000511 Madelung indole synthesis RXNO:0000511 Reaction of an N-(2-alkylphenyl)alkanamide with strong base to form an indole. https://orcid.org/0000-0001-5985-7429 Reaction of a N-(2-alkylphenyl)-trimethylsilylamine with two equivalents of organolithium and an ester or carboxylic acid to form an indole. batchelorc 2014-03-07T09:00:00Z Smith-modified Madelung synthesis RXNO RXNO:0000512 Smith indole synthesis RXNO:0000512 Reaction of a N-(2-alkylphenyl)-trimethylsilylamine with two equivalents of organolithium and an ester or carboxylic acid to form an indole. https://orcid.org/0000-0001-5985-7429 Rearrangement of an acyl imidate to form a carboximide. batchelorc 2014-03-07T09:00:00Z https://www.wikidata.org/wiki/Q723311 RXNO RXNO:0000513 Mumm rearrangement RXNO:0000513 Rearrangement of an acyl imidate to form a carboximide. https://orcid.org/0000-0001-5985-7429 Rearrangement of an aryl imino ether to yield an N,N-diaryl amide. batchelorc 2014-03-07T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r74/ RXNO RXNO:0000514 Chapman rearrangement RXNO:0000514 Rearrangement of an aryl imino ether to yield an N,N-diaryl amide. https://orcid.org/0000-0001-5985-7429 Reaction of an acetylated amino acid with an aldehyde then with a second amino acid, then hydrogenation and hydrolysis to form a dipeptide. It proceeds via an azlactone intermediate. batchelorc 2014-03-10T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r38/ RXNO RXNO:0000515 Bergmann azlactone peptide synthesis RXNO:0000515 Reaction of an acetylated amino acid with an aldehyde then with a second amino acid, then hydrogenation and hydrolysis to form a dipeptide. It proceeds via an azlactone intermediate. https://orcid.org/0000-0001-5985-7429 Removal of a terminal amino acid residue from a peptide by benzoylation, azidation, treatment with benzyl alcohol, hydrogenation and hydrolysis. batchelorc 2014-03-11T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r39/ RXNO RXNO:0000516 Bergmann degradation RXNO:0000516 Removal of a terminal amino acid residue from a peptide by benzoylation, azidation, treatment with benzyl alcohol, hydrogenation and hydrolysis. https://orcid.org/0000-0001-5985-7429 Removal of a terminal amino acid residue from a peptide. batchelorc 2014-03-11T09:00:00Z RXNO RXNO:0000517 terminal amino-acid residue cleaving reaction RXNO:0000517 Removal of a terminal amino acid residue from a peptide. https://orcid.org/0000-0001-5985-7429 Ring formation reaction where the intended product is an acridine. batchelorc 2014-03-12T09:00:00Z RXNO RXNO:0000518 acridine synthesis RXNO:0000518 Ring formation reaction where the intended product is an acridine. RSC:xp Reaction of a diarylamine in an organic acid or anhydride in the presence of zinc chloride to yield a 9-substituted acridine. batchelorc 2014-03-12T09:00:00Z doi:10.1039/b204243f https://www.rsc.org/Merck-Index/reaction/r41/ Bernthsen reaction RXNO RXNO:0000519 Definition source Merck Index, modified for errors. Bernthsen acridine synthesis RXNO:0000519 Reaction of a diarylamine in an organic acid or anhydride in the presence of zinc chloride to yield a 9-substituted acridine. https://orcid.org/0000-0001-5985-7429 Ring formation reaction where the intended product is a pyridine. batchelorc 2014-03-12T09:00:00Z RXNO RXNO:0000520 pyridine synthesis RXNO:0000520 Ring formation reaction where the intended product is a pyridine. RSC:xp Ring formation reaction where the intended product is a carbazole. batchelorc 2014-03-12T09:00:00Z RXNO RXNO:0000521 carbazole synthesis RXNO:0000521 Ring formation reaction where the intended product is a carbazole. RSC:xp Reaction of a phenol, an aromatic aldehyde and a primary aromatic or heterocyclic amine to yield a Betti's base, also known as an alpha-aminobenzylphenol. batchelorc 2014-03-13T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r42/ Betti synthesis RXNO RXNO:0000522 Betti reaction RXNO:0000522 Reaction of a phenol, an aromatic aldehyde and a primary aromatic or heterocyclic amine to yield a Betti's base, also known as an alpha-aminobenzylphenol. https://orcid.org/0000-0001-5985-7429 Reaction of a terminal hydroxyketone or terminal halogenoketone with an aromatic amine to yield a 2-substituted indole. batchelorc 2014-03-13T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r45/ Bischler reaction Bischler-Mohlau indole synthesis Bischler-Mohlau reaction Bischler-Möhlau reaction RXNO RXNO:0000523 Originally this involved a solvent but this need not be the case, see for example doi:10.1039/b719641e Bischler-Möhlau indole synthesis RXNO:0000523 Reaction of a terminal hydroxyketone or terminal halogenoketone with an aromatic amine to yield a 2-substituted indole. https://orcid.org/0000-0001-5985-7429 Cyclisation of an o-acylaminoacetophenone in alcoholic sodium hydroxide to form a substituted hydroxyquinoline. batchelorc 2014-03-24T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r70/ Camps cyclisation Camps cyclization RXNO RXNO:0000524 The substituent on the amino nitrogen can affect the ratio of 1-hydroxy to 3-hydroxy products. Camps quinoline synthesis RXNO:0000524 Cyclisation of an o-acylaminoacetophenone in alcoholic sodium hydroxide to form a substituted hydroxyquinoline. https://orcid.org/0000-0001-5985-7429 Palladium-catalysed coupling of copper(I) acetylides with aryl halides to yield arylacetylenes. batchelorc 2014-03-25T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r73/ RXNO RXNO:0000525 Castro-Stephens coupling RXNO:0000525 Palladium-catalysed coupling of copper(I) acetylides with aryl halides to yield arylacetylenes. https://orcid.org/0000-0001-5985-7429 Reaction of carbonyl compounds with ammonia or an amine to yield a pyridine. batchelorc 2014-03-25T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r75/ RXNO RXNO:0000526 Chichibabin pyridine synthesis RXNO:0000526 Reaction of carbonyl compounds with ammonia or an amine to yield a pyridine. https://orcid.org/0000-0001-5985-7429 Reaction of an azacycle with an alkali-metal amide to yield an aminated azacycle. batchelorc 2014-03-25T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r76/ RXNO RXNO:0000527 Chichibabin reaction RXNO:0000527 Reaction of an azacycle with an alkali-metal amide to yield an aminated azacycle. https://orcid.org/0000-0001-5985-7429 Reaction of a carboxylic ester with a magnesium iodide alkylamide to yield a carboxamide. batchelorc 2014-03-27T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r52/ RXNO RXNO:0000528 Bodroux reaction RXNO:0000528 Reaction of a carboxylic ester with a magnesium iodide alkylamide to yield a carboxamide. https://orcid.org/0000-0001-5985-7429 Condensation of beta-phenylethylmagnesium bromide with a cyclohexanone followed by cyclisation and dehydration in concentrated sulfuric acid to yield an octahydrophenanthrene. batchelorc 2014-03-27T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r53/ RXNO RXNO:0000529 Bogert-Cook synthesis RXNO:0000529 Condensation of beta-phenylethylmagnesium bromide with a cyclohexanone followed by cyclisation and dehydration in concentrated sulfuric acid to yield an octahydrophenanthrene. https://orcid.org/0000-0001-5985-7429 Reaction of a hydroxylated anthraquinone with fuming sulfuric acid or sulfuric acid in boric acid in the presence of a mercury or selenium catalyst to form a more hydroxylated anthraquinone. batchelorc 2014-03-27T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r54/ RXNO RXNO:0000530 Bohn-Schmidt reaction RXNO:0000530 Reaction of a hydroxylated anthraquinone with fuming sulfuric acid or sulfuric acid in boric acid in the presence of a mercury or selenium catalyst to form a more hydroxylated anthraquinone. https://orcid.org/0000-0001-5985-7429 Etherification of an aldehyde followed by bromination and reaction with a Grignard reagent followed by treatment with zinc to eliminate the halogen and alkoxy groups to produce an olefin. batchelorc 2014-03-27T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r55/ RXNO RXNO:0000531 Boord olefin synthesis RXNO:0000531 Etherification of an aldehyde followed by bromination and reaction with a Grignard reagent followed by treatment with zinc to eliminate the halogen and alkoxy groups to produce an olefin. https://orcid.org/0000-0001-5985-7429 Rearrangement of a cyclohexanone phenylhydrazone followed by oxidation to yield a carbazole. batchelorc 2014-03-27T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r56/ Borsche-Drechsel carbazole synthesis Borsche-Drechsel cyclization RXNO RXNO:0000532 Borsche-Drechsel cyclisation RXNO:0000532 Rearrangement of a cyclohexanone phenylhydrazone followed by oxidation to yield a carbazole. https://orcid.org/0000-0001-5985-7429 Reaction of an organomagnesium or organolithium compound with an N,N'-disubstituted formamide to yield the next homologous aldehyde. batchelorc 2014-03-27T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r57/ RXNO RXNO:0000533 Bouveault aldehyde synthesis RXNO:0000533 Reaction of an organomagnesium or organolithium compound with an N,N'-disubstituted formamide to yield the next homologous aldehyde. https://orcid.org/0000-0001-5985-7429 Diels-Alder reaction of a dienophile with a cationic aromatic azadiene to yield a bridged-ring system. batchelorc 2014-03-27T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r60/ Bradsher cyclization Bradsher cycloaddition RXNO RXNO:0000534 Bradsher cyclisation RXNO:0000534 Diels-Alder reaction of a dienophile with a cationic aromatic azadiene to yield a bridged-ring system. https://orcid.org/0000-0001-5985-7429 Reaction of an ortho-acyldiarylmethane, catalysed by acid, to yield an anthracene. batchelorc 2014-04-08T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r61/ RXNO RXNO:0000535 Bradsher reaction RXNO:0000535 Reaction of an ortho-acyldiarylmethane, catalysed by acid, to yield an anthracene. https://orcid.org/0000-0001-5985-7429 Reaction of a bromoarene that has an electrophilic group at the para-position with lithium bromide or lithium iodide followed by intramolecular cyclisation to yield a fused-ring system. batchelorc 2014-04-08T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r317/ RXNO RXNO:0000536 Parham cyclisation RXNO:0000536 Reaction of a bromoarene that has an electrophilic group at the para-position with lithium bromide or lithium iodide followed by intramolecular cyclisation to yield a fused-ring system. https://orcid.org/0000-0001-5985-7429 Reaction of an aliphatic aldehyde with a phenolic ether and hydrochloric acid to yield an alpha-chloroalkylphenolic ether. batchelorc 2014-04-14T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r357/ RXNO RXNO:0000537 Quelet reaction RXNO:0000537 Reaction of an aliphatic aldehyde with a phenolic ether and hydrochloric acid to yield an alpha-chloroalkylphenolic ether. https://orcid.org/0000-0001-5985-7429 Elimination of a water molecule from a secondary alcohol to yield an olefin. batchelorc 2014-04-14T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r77/ RXNO RXNO:0000538 Chugaev reaction RXNO:0000538 Elimination of a water molecule from a secondary alcohol to yield an olefin. https://orcid.org/0000-0001-5985-7429 Elimination of a hydroxylamine from an amine oxide by pyrolysis to yield an olefin. batchelorc 2014-04-14T09:00:00Z https://www.rsc.org/Merck-Index/reaction/r85/ https://www.wikidata.org/wiki/Q900370 Cope reaction RXNO RXNO:0000539 Cope elimination RXNO:0000539 Elimination of a hydroxylamine from an amine oxide by pyrolysis to yield an olefin. https://orcid.org/0000-0001-5985-7429 Reaction of an aniline with a nitrile in the presence of boron trichloride and a Lewis acid to yield an ortho-acylated aniline. batchelorc 2014-04-14T13:00:00Z https://www.rsc.org/Merck-Index/reaction/r423/ RXNO RXNO:0000540 Sugasawa reaction RXNO:0000540 Reaction of an aniline with a nitrile in the presence of boron trichloride and a Lewis acid to yield an ortho-acylated aniline. https://orcid.org/0000-0001-5985-7429 A cross-coupling reaction between a Grignard reagent and an activated (aryl or vinyl) halide or triflate. The reaction is catalysed by a palladium catalyst. batchelorc 2014-04-14T13:00:00Z RXNO RXNO:0000541 palladium-catalysed Kumada coupling RXNO:0000541 A cross-coupling reaction between a Grignard reagent and an activated (aryl or vinyl) halide or triflate. The reaction is catalysed by a palladium catalyst. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 A cross-coupling reaction between a Grignard reagent and an activated (aryl or vinyl) halide or triflate. The reaction is catalysed by a nickel catalyst. batchelorc 2014-04-14T13:00:00Z RXNO RXNO:0000542 nickel-catalysed Kumada coupling RXNO:0000542 A cross-coupling reaction between a Grignard reagent and an activated (aryl or vinyl) halide or triflate. The reaction is catalysed by a nickel catalyst. RSC:db https://orcid.org/0000-0001-5985-7429 https://orcid.org/0000-0002-4077-4719 Reaction of a 1,2-diol with triethoxymethane under heat to yield an olefin. batchelorc 2014-04-15T11:00:00Z https://www.rsc.org/Merck-Index/reaction/r121/ RXNO RXNO:0000543 The reaction is stereospecific. It proceeds via a 1,3-dioxolane intermediate. Eastwood reaction RXNO:0000543 Reaction of a 1,2-diol with triethoxymethane under heat to yield an olefin. https://orcid.org/0000-0001-5985-7429 Reaction of silyl enol ethers with palladium acetate in acetonitrile to yield an alpha,beta-unsaturated ketone. batchelorc 2014-04-22T16:00:00Z https://www.rsc.org/Merck-Index/reaction/r382/ RXNO RXNO:0000544 Saegusa oxidation RXNO:0000544 Reaction of silyl enol ethers with palladium acetate in acetonitrile to yield an alpha,beta-unsaturated ketone. doi:10.1021/jo00399a052 Reaction of diphenylthiourea with lead carbonate and potassium cyanide to form a cyanoformidine followed by ring closure and acid hydrolysis to yield isatin. batchelorc 2014-04-24T15:00:00Z https://www.rsc.org/Merck-Index/reaction/r384/ RXNO RXNO:0000545 Sandmeyer diphenylurea isatin synthesis RXNO:0000545 Reaction of diphenylthiourea with lead carbonate and potassium cyanide to form a cyanoformidine followed by ring closure and acid hydrolysis to yield isatin. https://orcid.org/0000-0001-5985-7429 Reaction of aniline, hydroxylamine and chloral hydrate to form an aniline intermediate followed by cyclization in acid and hydrolysis to yield isatin. batchelorc 2014-04-24T15:00:00Z https://www.rsc.org/Merck-Index/reaction/r385/ RXNO RXNO:0000546 Sandmeyer isonitrosoacetanilide isatin synthesis RXNO:0000546 Reaction of aniline, hydroxylamine and chloral hydrate to form an aniline intermediate followed by cyclization in acid and hydrolysis to yield isatin. https://orcid.org/0000-0001-5985-7429 Oxidation of an alcohol with a pyridine-chromium trioxide complex to yield a carbonyl compound. batchelorc 2014-04-24T15:00:00Z https://www.rsc.org/Merck-Index/reaction/r387/ RXNO RXNO:0000547 Sarett oxidation RXNO:0000547 Oxidation of an alcohol with a pyridine-chromium trioxide complex to yield a carbonyl compound. https://orcid.org/0000-0001-5985-7429 Oxidation of a primary alcohol with a pyridine-chromium trioxide complex to yield an aldehyde. batchelorc 2014-04-24T15:00:00Z https://www.wikidata.org/wiki/Q2227511 RXNO RXNO:0000548 Sarett primary alcohol oxidation RXNO:0000548 Oxidation of a primary alcohol with a pyridine-chromium trioxide complex to yield an aldehyde. https://orcid.org/0000-0001-5985-7429 Oxidation of a secondary alcohol with a pyridine-chromium trioxide complex to yield a ketone. batchelorc 2014-04-24T15:00:00Z RXNO RXNO:0000549 Sarett secondary alcohol oxidation RXNO:0000549 Oxidation of a secondary alcohol with a pyridine-chromium trioxide complex to yield a ketone. https://orcid.org/0000-0001-5985-7429 Oxidation of a primary alcohol with a pyridine-chromium trioxide complex in dichloromethane to yield an aldehyde. batchelorc 2014-04-24T15:00:00Z https://www.rsc.org/Merck-Index/reaction/r387/ RXNO RXNO:0000550 Collins oxidation RXNO:0000550 Oxidation of a primary alcohol with a pyridine-chromium trioxide complex in dichloromethane to yield an aldehyde. https://orcid.org/0000-0001-5985-7429 A functional group modification where a carbonyl oxygen is replaced by an imine. RXNO RXNO:0000551 reductive imination RXNO:0000551 A functional group modification where a carbonyl oxygen is replaced by an imine. https://orcid.org/0000-0001-5985-7429 Reductive amination of an aldehyde with ammonium formate or formamide to form an amine. RXNO RXNO:0000552 Leuckart aldehyde reaction RXNO:0000552 Reductive amination of an aldehyde with ammonium formate or formamide to form an amine. https://orcid.org/0000-0001-5985-7429 Reductive amination of a ketone with ammonium formate or formamide to form an amine. RXNO RXNO:0000553 Leuckart ketone reaction RXNO:0000553 Reductive amination of a ketone with ammonium formate or formamide to form an amine. https://orcid.org/0000-0001-5985-7429 Conversion of an alcohol to an alkyl bromide with triphenylphosphine and tetrabromomethane. RXNO RXNO:0000554 Appel bromination with tetrabromomethane RXNO:0000554 Conversion of an alcohol to an alkyl bromide with triphenylphosphine and tetrabromomethane. https://orcid.org/0000-0001-5985-7429 Conversion of an alcohol to an alkyl bromide with triphenylphosphine and bromine. RXNO RXNO:0000555 Appel bromination with bromine RXNO:0000555 Conversion of an alcohol to an alkyl bromide with triphenylphosphine and bromine. https://orcid.org/0000-0001-5985-7429 Reaction of an aldehyde with tetrabromomethane and triphenylphosphine to yield a terminal dibromoolefin. Corey-Fuchs reaction step 1 RXNO RXNO:0000556 This is the first step of the Corey-Fuchs reaction. The second step is the Fritsch-Buttenberg-Wiechell rearrangement. Corey-Fuchs terminal dibromoolefination RXNO:0000556 Reaction of an aldehyde with tetrabromomethane and triphenylphosphine to yield a terminal dibromoolefin. https://orcid.org/0000-0001-5985-7429 RXNO RXNO:0000557 This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000624 for Heck-type reaction and RXNO:0000603 for cross-coupling. obsolete: Heck-type reaction/cross-coupling true RXNO:0000557 RXNO RXNO:0000558 This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000625 for the bromo Heck reaction and RXNO:0000604 for Liebeskind-Srogl coupling. obsolete: bromo Heck reaction/Liebeskind-Srogl coupling true RXNO:0000558 RXNO RXNO:0000559 This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000626 for the chloro Heck reaction and RXNO:0000605 for Fukuyama coupling. obsolete: chloro Heck reaction/Fukuyama coupling true RXNO:0000559 RXNO RXNO:0000560 This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000627 for the iodo Heck reaction and RXNO:0000606 for the chloride Finkelstein reaction. obsolete: iodo Heck reaction/chloride Finkelstein reaction true RXNO:0000560 RXNO RXNO:0000561 This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000628 for the triflyloxy Heck reaction and RXNO:0000607 for the bromide Finkelstein reaction. obsolete: triflyloxy Heck reaction/bromide Finkelstein reaction true RXNO:0000561 RXNO RXNO:0000562 This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000629 for the bromo Heck-type reaction and RXNO:0000608 for the sulfonate ester Finkelstein reaction. obsolete: bromo Heck-type reaction/sulfonate ester Finkelstein reaction true RXNO:0000562 RXNO RXNO:0000563 This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000630 for the chloro Heck-type reaction and RXNO:0000609 for Sandmeyer fluorination. obsolete: chloro Heck-type reaction/Sandmeyer fluorination true RXNO:0000563 RXNO RXNO:0000564 This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000631 for acyclic Beckmann rearrangement and RXNO:0000610 for Sandmeyer chlorination. obsolete: acyclic Beckmann rearrangement/Sandmeyer chlorination true RXNO:0000564 RXNO RXNO:0000565 This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000632 for Baeyer-Emmerling indole synthesis and RXNO:0000611 for Sandmeyer bromination. obsolete: Baeyer–Emmerling indole synthesis/Sandmeyer bromination true RXNO:0000565 RXNO RXNO:0000566 This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000633 for bromo Sonogashira coupling and RXNO:0000612 for Sandmeyer iodination. obsolete: bromo Sonogashira coupling/Sandmeyer iodination true RXNO:0000566 RXNO RXNO:0000567 This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000634 for bromo Suzuki coupling and RXNO:0000613 for the iodo Heck reaction. obsolete: bromo Suzuki coupling/iodo Heck reaction true RXNO:0000567 RXNO RXNO:0000568 This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000635 for bromo Suzuki-type coupling and RXNO:0000628 for the triflyloxy Heck reaction. obsolete: bromo Suzuki-type coupling/triflyloxy Heck reaction true RXNO:0000568 RXNO RXNO:0000569 This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000636 for bromolactonization and RXNO:0000629 for the bromo Heck-type reaction. obsolete: bromolactonization/bromo Heck-type reaction true RXNO:0000569 RXNO RXNO:0000570 This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000637 for chloro Sonogashira coupling and RXNO:0000630 for the chloro Heck-type reaction. obsolete: chloro Sonogashira coupling/chloro Heck-type reaction true RXNO:0000570 RXNO RXNO:0000571 This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000638 for chloro Suzuki coupling and RXNO:0000624 for the Heck-type reaction. obsolete: chloro Suzuki coupling/Heck-type reaction true RXNO:0000571 RXNO RXNO:0000572 This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000639 for chloro Suzuki-type coupling and RXNO:0000625 for the bromo Heck reaction. obsolete: chloro Suzuki-type coupling/bromo Heck reaction true RXNO:0000572 RXNO RXNO:0000573 This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000640 for chlorolactonization and RXNO:0000626 for the chloro Heck reaction. obsolete: chlorolactonization/chloro Heck reaction true RXNO:0000573 A Beckmann rearrangement which produces a cyclic product. NAMERXN:4.1.6 RXNO RXNO:0000574 cyclic Beckmann rearrangement RXNO:0000574 A Beckmann rearrangement which produces a cyclic product. https://orcid.org/0000-0001-5985-7429 A Dess-Martin oxidation of a primary alcohol to an aldehyde. NAMERXN:8.1.2 aldehyde Dess-Martin oxidation RXNO RXNO:0000575 Dess-Martin aldehyde oxidation RXNO:0000575 A Dess-Martin oxidation of a primary alcohol to an aldehyde. https://orcid.org/0000-0001-5985-7429 A Dess-Martin oxidation of a secondary alcohol to a ketone. NAMERXN:8.1.3 ketone Dess-Martin oxidation RXNO RXNO:0000576 Dess-Martin ketone oxidation RXNO:0000576 A Dess-Martin oxidation of a secondary alcohol to a ketone. https://orcid.org/0000-0001-5985-7429 Synthesis of a quinoline by reaction of a 2-aminobenzaldehyde with a ketone. NAMERXN:4.1.29 https://www.wikidata.org/wiki/Q1058388 Friedlaender synthesis Friedlander synthesis Friedländer synthesis RXNO RXNO:0000577 Friedlander quinoline synthesis RXNO:0000577 Synthesis of a quinoline by reaction of a 2-aminobenzaldehyde with a ketone. https://orcid.org/0000-0001-5985-7429 Reaction of an aldehyde or ketone with an alpha-cyanoester to form a 2-aminothiophene. NAMERXN:4.3.4 https://www.wikidata.org/wiki/Q240091 Gewald thiophene synthesis RXNO RXNO:0000578 Gewald reaction RXNO:0000578 Reaction of an aldehyde or ketone with an alpha-cyanoester to form a 2-aminothiophene. https://orcid.org/0000-0001-5985-7429 A Sonogashira coupling where the aryl halide is an aryl iodide. NAMERXN:3.3.4 RXNO RXNO:0000579 iodo Sonogashira coupling RXNO:0000579 A Sonogashira coupling where the aryl halide is an aryl iodide. https://orcid.org/0000-0001-5985-7429 A Suzuki coupling where the halide is an iodide. NAMERXN:3.1.3 iodo Suzuki-Miyaura coupling RXNO RXNO:0000580 iodo Suzuki coupling RXNO:0000580 A Suzuki coupling where the halide is an iodide. https://orcid.org/0000-0001-5985-7429 A Suzuki-type coupling where the halide is an iodide. NAMERXN:3.1.7 iodo Suzuki-Miyaura-type coupling RXNO RXNO:0000581 iodo Suzuki-type coupling RXNO:0000581 A Suzuki-type coupling where the halide is an iodide. https://orcid.org/0000-0001-5985-7429 A halolactionization where the halide is an iodide. NAMERXN:4.2.15 https://www.wikidata.org/wiki/Q6062283 iodolactonisation RXNO RXNO:0000582 iodolactonization RXNO:0000582 A halolactionization where the halide is an iodide. https://orcid.org/0000-0001-5985-7429 An azacycle synthesis where the product is a 4-oxo-3,4-dihydroquinazoline and the reactants are a 2-aminobenzoic acid and an amide. NAMERXN:4.1.30 https://www.wikidata.org/wiki/Q1059542 RXNO RXNO:0000583 Niementowski quinazoline synthesis RXNO:0000583 An azacycle synthesis where the product is a 4-oxo-3,4-dihydroquinazoline and the reactants are a 2-aminobenzoic acid and an amide. https://orcid.org/0000-0001-5985-7429 A quinoline synthesis where the product is a gamma-hydroxyquinoline and the reactants are a 2-aminobenzoic acid and an aldehyde or ketone. NAMERXN:4.1.31 https://www.wikidata.org/wiki/Q2733837 RXNO RXNO:0000584 Niementowski quinoline synthesis RXNO:0000584 A quinoline synthesis where the product is a gamma-hydroxyquinoline and the reactants are a 2-aminobenzoic acid and an aldehyde or ketone. https://orcid.org/0000-0001-5985-7429 An azacycle synthesis where the product is an isoquinoline and the reactants are a benzaldehyde and a 2,2-dialkoxyethylamine. NAMERXN:4.1.65 https://www.wikidata.org/wiki/Q18217151 Pomeranz–Fritsch cyclization Pomeranz–Fritsch isoquinoline synthesis RXNO RXNO:0000585 Pomeranz–Fritsch reaction RXNO:0000585 An azacycle synthesis where the product is an isoquinoline and the reactants are a benzaldehyde and a 2,2-dialkoxyethylamine. https://orcid.org/0000-0001-5985-7429 An O-acylation to ester where dicyclohexylcarbodiimide is used as a coupling reagent and 4-dimethylaminopyridine as a catalyst. NAMERXN:2.6.9 https://www.wikidata.org/wiki/Q695687 RXNO RXNO:0000586 Steglich esterification RXNO:0000586 An O-acylation to ester where dicyclohexylcarbodiimide is used as a coupling reagent and 4-dimethylaminopyridine as a catalyst. https://orcid.org/0000-0001-5985-7429 A Sonogashira coupling where the role of the halide is played by a triflyloxy group. NAMERXN:3.3.5 Triflyloxy Sonogashira coupling RXNO RXNO:0000587 triflyloxy Sonogashira coupling RXNO:0000587 A Sonogashira coupling where the role of the halide is played by a triflyloxy group. https://orcid.org/0000-0001-5985-7429 A Suzuki coupling where the rule of the halide is played by a triflyloxy group. NAMERXN:3.1.4 Triflyloxy Suzuki coupling triflyloxy Suzuki-Miyaura coupling RXNO RXNO:0000588 triflyloxy Suzuki coupling RXNO:0000588 A Suzuki coupling where the rule of the halide is played by a triflyloxy group. https://orcid.org/0000-0001-5985-7429 A Suzuki-type coupling where the rule of the halide is played by a triflyloxy group. NAMERXN:3.1.8 Triflyloxy Suzuki-type coupling triflyloxy Suzuki-Miyaura-type coupling RXNO RXNO:0000589 triflyloxy Suzuki-type coupling RXNO:0000589 A Suzuki-type coupling where the rule of the halide is played by a triflyloxy group. https://orcid.org/0000-0001-5985-7429 Synthesis of an aziridine by dehydrating a beta aminoalcohol with sulfuric acid. NAMERXN:4.1.66 https://doi.org/10.1021/ja01314a504 https://www.wikidata.org/wiki/Q900233 Wenker aziridine synthesis RXNO RXNO:0000590 Wenker synthesis RXNO:0000590 Synthesis of an aziridine by dehydrating a beta aminoalcohol with sulfuric acid. https://orcid.org/0000-0001-5985-7429 Reaction of an alpha-diketone with a dialkyl thiodiacetate to form a thiophene dicarboxylic acid. https://www.rsc.org/Merck-Index/reaction/r202/ https://www.wikidata.org/wiki/Q18020904 RXNO RXNO:0000591 Hinsberg thiophene synthesis RXNO:0000591 Reaction of an alpha-diketone with a dialkyl thiodiacetate to form a thiophene dicarboxylic acid. https://orcid.org/0000-0001-5985-7429 The coupling of a boronic acid or boronic ester with an unsaturated halide, triflate or sulfonate. RXNO RXNO:0000592 Suzuki-type coupling RXNO:0000592 The coupling of a boronic acid or boronic ester with an unsaturated halide, triflate or sulfonate. https://orcid.org/0000-0001-5985-7429 Addition of a carboxylic acid oxygen and halogen across a carbon-carbon double bond to form a lactone. halolactonisation RXNO RXNO:0000593 halolactonization RXNO:0000593 Addition of a carboxylic acid oxygen and halogen across a carbon-carbon double bond to form a lactone. https://orcid.org/0000-0001-5985-7429 Expansion of a pyrrole ring by heating with a halogeno compond to form a 3-halogenopyridine. https://www.rsc.org/Merck-Index/reaction/r78/ https://www.wikidata.org/wiki/Q6151790 RXNO RXNO:0000594 Ciamician-Dennstedt rearrangement RXNO:0000594 Expansion of a pyrrole ring by heating with a halogeno compond to form a 3-halogenopyridine. https://orcid.org/0000-0001-5985-7429 Condensation of an aromatic aldehyde with an aliphatic aldehyde or ketone in the presence of a relatively strong base to from an alpha,beta-unsaturated aldehyde or ketone. https://www.rsc.org/Merck-Index/reaction/r81/ https://www.wikidata.org/wiki/Q56298266 RXNO RXNO:0000595 Claisen-Schmidt condensation RXNO:0000595 Condensation of an aromatic aldehyde with an aliphatic aldehyde or ketone in the presence of a relatively strong base to from an alpha,beta-unsaturated aldehyde or ketone. https://orcid.org/0000-0001-5985-7429 RXNO RXNO:0000596 this ID has been obsoleted because it was used for two different classes. obsolete: Combes quinoline synthesis/Conrad%E2%80%93Limpach_synthesis true RXNO:0000596 Enantioselective reduction of a ketone to an alcohol with a chiral oxazaborolidine. https://www.rsc.org/Merck-Index/reaction/r87/ https://www.wikidata.org/wiki/Q903598 CBS reduction Corey-Itsuno reduction RXNO RXNO:0000597 Corey-Bakshi-Shibata reduction RXNO:0000597 Enantioselective reduction of a ketone to an alcohol with a chiral oxazaborolidine. https://orcid.org/0000-0001-5985-7429 Reaction of a sulfur ylide with a double-bond to produce a three-membered ring. https://www.rsc.org/Merck-Index/reaction/r88/ https://www.wikidata.org/wiki/Q1582682 Corey-Chaykovsky reaction RXNO RXNO:0000598 Johnson-Corey-Chaykovsky reaction RXNO:0000598 Reaction of a sulfur ylide with a double-bond to produce a three-membered ring. https://orcid.org/0000-0001-5985-7429 Reaction of a sulfur ylide with a ketone to produce an epoxide. RXNO RXNO:0000599 Johnson-Corey-Chaykovsky epoxide synthesis RXNO:0000599 Reaction of a sulfur ylide with a ketone to produce an epoxide. https://orcid.org/0000-0001-5985-7429 Reaction of a sulfur ylide with an olefin to produce a cyclopropane. RXNO RXNO:0000600 Johnson-Corey-Chaykovsky cyclopropane synthesis RXNO:0000600 Reaction of a sulfur ylide with an olefin to produce a cyclopropane. https://orcid.org/0000-0001-5985-7429 Reaction of a sulfur ylide with an imine to produce an aziridine. RXNO RXNO:0000601 Johnson-Corey-Chaykovsky aziridine synthesis RXNO:0000601 Reaction of a sulfur ylide with an imine to produce an aziridine. https://orcid.org/0000-0001-5985-7429 Reaction of a sulfur ylide with a thione to produce a thiirane. RXNO RXNO:0000602 Johnson-Corey-Chaykovsky thiirane synthesis RXNO:0000602 Reaction of a sulfur ylide with a thione to produce a thiirane. https://orcid.org/0000-0001-5985-7429 A joining reaction where a carbon-carbon bond is formed between unlike moieties. https://www.wikidata.org/wiki/Q7127709 RXNO RXNO:0000603 cross-coupling RXNO:0000603 A joining reaction where a carbon-carbon bond is formed between unlike moieties. https://orcid.org/0000-0001-5985-7429 A cross-coupling reaction where a thioester and a boronic acid react to form a ketone. It uses a metal catalyst. https://www.wikidata.org/wiki/Q6543886 RXNO RXNO:0000604 Liebeskind-Srogl coupling RXNO:0000604 A cross-coupling reaction where a thioester and a boronic acid react to form a ketone. It uses a metal catalyst. https://orcid.org/0000-0001-5985-7429 A cross-coupling reaction where a thioester and an organozinc halide react to form a ketone. It uses a palladium catalyst. https://www.wikidata.org/wiki/Q5507762 RXNO RXNO:0000605 Fukuyama coupling RXNO:0000605 A cross-coupling reaction where a thioester and an organozinc halide react to form a ketone. It uses a palladium catalyst. https://orcid.org/0000-0001-5985-7429 The conversion of an alkyl chloride to an alkyl iodide by SN2 substitution.The reaction relies upon the equilibrium being pushed to completion by precipitation. RXNO RXNO:0000606 chloride Finkelstein reaction RXNO:0000606 The conversion of an alkyl chloride to an alkyl iodide by SN2 substitution.The reaction relies upon the equilibrium being pushed to completion by precipitation. https://orcid.org/0000-0001-5985-7429 The conversion of an alkyl bromide to an alkyl iodide by SN2 substitution.The reaction relies upon the equilibrium being pushed to completion by precipitation. RXNO RXNO:0000607 bromide Finkelstein reaction RXNO:0000607 The conversion of an alkyl bromide to an alkyl iodide by SN2 substitution.The reaction relies upon the equilibrium being pushed to completion by precipitation. https://orcid.org/0000-0001-5985-7429 The conversion of an alkyl sulfonate ester to an alkyl iodide by SN2 substitution.The reaction relies upon the equilibrium being pushed to completion by precipitation. RXNO RXNO:0000608 sulfonate ester Finkelstein reaction RXNO:0000608 The conversion of an alkyl sulfonate ester to an alkyl iodide by SN2 substitution.The reaction relies upon the equilibrium being pushed to completion by precipitation. https://orcid.org/0000-0001-5985-7429 An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) fluoride to form an aromatic fluoride. RXNO RXNO:0000609 Sandmeyer fluorination RXNO:0000609 An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) fluoride to form an aromatic fluoride. https://orcid.org/0000-0001-5985-7429 An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) chloride to form an aromatic chloride. RXNO RXNO:0000610 Sandmeyer chlorination RXNO:0000610 An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) chloride to form an aromatic chloride. https://orcid.org/0000-0001-5985-7429 An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) bromide to form an aromatic bromide. RXNO RXNO:0000611 Sandmeyer bromination RXNO:0000611 An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) bromide to form an aromatic bromide. https://orcid.org/0000-0001-5985-7429 An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) iodide to form an aromatic iodide. RXNO RXNO:0000612 Sandmeyer iodination RXNO:0000612 An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) iodide to form an aromatic iodide. https://orcid.org/0000-0001-5985-7429 A planned reaction in which one of the products contains an imidazole system that was not in any of the reactants. RXNO RXNO:0000613 imidazole synthesis RXNO:0000613 A planned reaction in which one of the products contains an imidazole system that was not in any of the reactants. https://orcid.org/0000-0001-5985-7429 A planned reaction in which one of the products contains an indazole system that was not in any of the reactants. RXNO RXNO:0000614 indazole synthesis RXNO:0000614 A planned reaction in which one of the products contains an indazole system that was not in any of the reactants. https://orcid.org/0000-0001-5985-7429 A planned reaction in which one of the products contains a piperazine system that was not in any of the reactants. RXNO RXNO:0000615 piperazine synthesis RXNO:0000615 A planned reaction in which one of the products contains a piperazine system that was not in any of the reactants. https://orcid.org/0000-0001-5985-7429 A planned reaction in which one of the products contains a piperidine system that was not in any of the reactants. RXNO RXNO:0000616 piperidine synthesis RXNO:0000616 A planned reaction in which one of the products contains a piperidine system that was not in any of the reactants. https://orcid.org/0000-0001-5985-7429 A planned reaction in which one of the products contains a pyrrolidine system that was not in any of the reactants. RXNO RXNO:0000617 pyrrolidine synthesis RXNO:0000617 A planned reaction in which one of the products contains a pyrrolidine system that was not in any of the reactants. https://orcid.org/0000-0001-5985-7429 An azacycle synthesis in which pyrrolidines or piperidines are formed by decomposition of protonated N-haloamines. https://www.rsc.org/Merck-Index/reaction/r207/ https://www.wikidata.org/wiki/Q5876831 Hofmann-Löffler reaction RXNO RXNO:0000618 Hofmann-Löffler-Freytag reaction RXNO:0000618 An azacycle synthesis in which pyrrolidines or piperidines are formed by decomposition of protonated N-haloamines. https://www.rsc.org/Merck-Index/reaction/r207/hofmann-löffler-freytag%20reaction A Hofmann-Löffler-Freytag reaction in which the product is a piperidine. RXNO RXNO:0000619 Hofmann-Löffler-Freytag piperidine synthesis RXNO:0000619 A Hofmann-Löffler-Freytag reaction in which the product is a piperidine. https://orcid.org/0000-0001-5985-7429 A Hofmann-Löffler-Freytag reaction in which the product is a pyrrolidine. RXNO RXNO:0000620 Hofmann-Löffler-Freytag pyrrolidine synthesis RXNO:0000620 A Hofmann-Löffler-Freytag reaction in which the product is a pyrrolidine. https://orcid.org/0000-0001-5985-7429 An alpha-halogenation reaction where a carboxylic acid reacts with dibromine to form an alpha-bromocarboxylic acid. https://www.rsc.org/Merck-Index/reaction/r194 https://www.wikidata.org/wiki/Q902219 Hell-Volhard-Zelinsky halogenation RXNO RXNO:0000621 Hell-Volhard-Zelinsky reaction RXNO:0000621 An alpha-halogenation reaction where a carboxylic acid reacts with dibromine to form an alpha-bromocarboxylic acid. https://orcid.org/0000-0001-5985-7429 Meerwein-Ponndorf-Verley reduction of an aldehyde to the corresponding primary alcohol. RXNO RXNO:0000622 Meerwein-Ponndorf-Verley reduction of an aldehyde RXNO:0000622 Meerwein-Ponndorf-Verley reduction of an aldehyde to the corresponding primary alcohol. https://orcid.org/0000-0001-5985-7429 Meerwein-Ponndorf-Verley reduction of a ketone to the corresponding secondary alcohol. RXNO RXNO:0000623 Meerwein-Ponndorf-Verley reduction of a ketone RXNO:0000623 Meerwein-Ponndorf-Verley reduction of a ketone to the corresponding secondary alcohol. https://orcid.org/0000-0001-5985-7429 A carbon-carbon coupling reaction where an organohalide or triflate couples to a terminal olefin to produce an internal olefin. RXNO RXNO:0000624 Heck-type reaction RXNO:0000624 A carbon-carbon coupling reaction where an organohalide or triflate couples to a terminal olefin to produce an internal olefin. RSC:db https://orcid.org/0000-0001-5985-7429 A Heck reaction where an organobromide couples to a terminal olefin to produce an internal olefin, catalysed by palladium. RXNO RXNO:0000625 obsolete: bromo Heck reaction true RXNO:0000625 A Heck reaction where an organobromide couples to a terminal olefin to produce an internal olefin, catalysed by palladium. RSC:db https://orcid.org/0000-0001-5985-7429 A Heck reaction where an organochloride couples to a terminal olefin to produce an internal olefin, catalysed by palladium. RXNO RXNO:0000626 chloro Heck reaction RXNO:0000626 A Heck reaction where an organochloride couples to a terminal olefin to produce an internal olefin, catalysed by palladium. RSC:db https://orcid.org/0000-0001-5985-7429 A Heck reaction where an organoiodide couples to a terminal olefin to produce an internal olefin, catalysed by palladium. RXNO RXNO:0000627 iodo Heck reaction RXNO:0000627 A Heck reaction where an organoiodide couples to a terminal olefin to produce an internal olefin, catalysed by palladium. RSC:db https://orcid.org/0000-0001-5985-7429 A Heck reaction where an organotriflate couples to a terminal olefin to produce an internal olefin, catalysed by palladium. RXNO RXNO:0000628 triflyloxy Heck reaction RXNO:0000628 A Heck reaction where an organotriflate couples to a terminal olefin to produce an internal olefin, catalysed by palladium. RSC:db https://orcid.org/0000-0001-5985-7429 A Heck-type reaction where an organobromide couples to a terminal olefin to produce an internal olefin. RXNO RXNO:0000629 bromo Heck-type reaction RXNO:0000629 A Heck-type reaction where an organobromide couples to a terminal olefin to produce an internal olefin. RSC:db https://orcid.org/0000-0001-5985-7429 A Heck-type reaction where an organochloride couples to a terminal olefin to produce an internal olefin. RXNO RXNO:0000630 chloro Heck-type reaction RXNO:0000630 A Heck-type reaction where an organochloride couples to a terminal olefin to produce an internal olefin. RSC:db https://orcid.org/0000-0001-5985-7429 A Beckmann rearrangement where an acyclic amide is formed. NAMERXN:2.8.1 RXNO RXNO:0000631 acyclic Beckmann rearrangement RXNO:0000631 A Beckmann rearrangement where an acyclic amide is formed. https://orcid.org/0000-0001-5985-7429 An indole synthesis where an ortho-nitrocinnamic acid reacts with iron powder in a basic solution to form an indole. NAMERXN:4.1.41 https://doi.org/10.1002/cber.186900201268 https://www.wikidata.org/wiki/Q3159940 RXNO RXNO:0000632 Baeyer–Emmerling indole synthesis RXNO:0000632 An indole synthesis where an ortho-nitrocinnamic acid reacts with iron powder in a basic solution to form an indole. https://orcid.org/0000-0001-5985-7429 A Sonogashira coupling where the aryl halide is an aryl bromide. NAMERXN:3.3.2 Bromo Sonogashira coupling RXNO RXNO:0000633 bromo Sonogashira coupling RXNO:0000633 A Sonogashira coupling where the aryl halide is an aryl bromide. https://orcid.org/0000-0001-5985-7429 A Suzuki coupling where the halide is a bromide. NAMERXN:3.1.1 Bromo Suzuki coupling bromo Suzuki-Miyaura coupling RXNO RXNO:0000634 bromo Suzuki coupling RXNO:0000634 A Suzuki coupling where the halide is a bromide. https://orcid.org/0000-0001-5985-7429 A Suzuki-type coupling where the halide is a bromide. NAMERXN:3.1.5 Bromo Suzuki-type coupling bromo Suzuki-Miyaura-type coupling RXNO RXNO:0000635 bromo Suzuki-type coupling RXNO:0000635 A Suzuki-type coupling where the halide is a bromide. https://orcid.org/0000-0001-5985-7429 A halolactionization where the halide is a bromide. NAMERXN:4.2.13 bromolactonisation RXNO RXNO:0000636 bromolactonization RXNO:0000636 A halolactionization where the halide is a bromide. https://orcid.org/0000-0001-5985-7429 A Sonogashira coupling where the aryl halide is an aryl chloride. NAMERXN:3.3.3 Chloro Sonogashira coupling RXNO RXNO:0000637 chloro Sonogashira coupling RXNO:0000637 A Sonogashira coupling where the aryl halide is an aryl chloride. https://orcid.org/0000-0001-5985-7429 A Suzuki coupling where the halide is a chloride. NAMERXN:3.1.2 Chloro Suzuki coupling chloro Suzuki-Miyaura coupling RXNO RXNO:0000638 chloro Suzuki coupling RXNO:0000638 A Suzuki coupling where the halide is a chloride. https://orcid.org/0000-0001-5985-7429 A Suzuki-type coupling where the halide is a chloride. NAMERXN:3.1.6 Chloro Suzuki-type coupling chloro Suzuki-Miyaura-type coupling RXNO RXNO:0000639 chloro Suzuki-type coupling RXNO:0000639 A Suzuki-type coupling where the halide is a chloride. https://orcid.org/0000-0001-5985-7429 A halolactionization where the halide is a chloride. NAMERXN:4.2.14 chlorolactonisation RXNO RXNO:0000640 chlorolactonization RXNO:0000640 A halolactionization where the halide is a chloride. https://orcid.org/0000-0001-5985-7429 Reaction of an arylamine wtih a beta-ketoester to yield a 4-hydroxyquinoline. https://en.wikipedia.org/wiki/Conrad%E2%80%93Limpach_synthesis https://www.rsc.org/Merck-Index/reaction/r84/ https://www.wikidata.org/wiki/Q1944895 Conrad-Limpach cyclization Conrad-Limpach synthesis RXNO RXNO:0000641 Conrad-Limpach cyclisation RXNO:0000641 Reaction of an arylamine wtih a beta-ketoester to yield a 4-hydroxyquinoline. https://orcid.org/0000-0001-5985-7429 Reaction of a beta-diketone with a primary arylamine to yield a quinoline. It is acid-catalysed. https://en.wikipedia.org/wiki/Combes_quinoline_synthesis https://www.rsc.org/Merck-Index/reaction/r83/ https://www.wikidata.org/wiki/Q1058068 RXNO RXNO:0000642 Combes quinoline synthesis RXNO:0000642 Reaction of a beta-diketone with a primary arylamine to yield a quinoline. It is acid-catalysed. https://orcid.org/0000-0001-5985-7429 A 1,3-dipolar cycloaddition reaction where a fullerene reacts with an aldehyde and an amino acid to form a pyrrolidinofullerene. https://www.wikidata.org/wiki/Q4391481 RXNO RXNO:0000643 Prato reaction RXNO:0000643 A 1,3-dipolar cycloaddition reaction where a fullerene reacts with an aldehyde and an amino acid to form a pyrrolidinofullerene. https://orcid.org/0000-0001-5985-7429 A rearrangement of a 2-furylcarbinol to a 4-hydroxycyclopentenone. It is acid-catalysed. https://www.wikidata.org/wiki/Q3319193 RXNO RXNO:0000644 Piancatelli rearrangement RXNO:0000644 A rearrangement of a 2-furylcarbinol to a 4-hydroxycyclopentenone. It is acid-catalysed. https://orcid.org/0000-0001-5985-7429 A ring-breaking reaction where a pyrrolidinofullerene yields a fullerene. The substituted fullerene is heated with a dipolarophile and a catalyst. RXNO RXNO:0000645 retro-Prato reaction RXNO:0000645 A ring-breaking reaction where a pyrrolidinofullerene yields a fullerene. The substituted fullerene is heated with a dipolarophile and a catalyst. https://doi.org/10.1002/anie.200502556 https://orcid.org/0000-0001-5985-7429 A cycloaddition where a fullerene reacts with diethyl bromomalonate to form a methanofullerene. https://www.wikidata.org/wiki/Q1054818 RXNO RXNO:0000646 Bingel reaction RXNO:0000646 A cycloaddition where a fullerene reacts with diethyl bromomalonate to form a methanofullerene. https://doi.org/10.1002/cber.19931260829 https://orcid.org/0000-0001-5985-7429 A cyclisation where a hydroxyl group acts as the nucleophile in a Wacker-Tsuji oxidation accompanied by beta-hydride elimination, forming a ring. Wacker cyclization RXNO RXNO:0000647 Wacker cyclisation RXNO:0000647 A cyclisation where a hydroxyl group acts as the nucleophile in a Wacker-Tsuji oxidation accompanied by beta-hydride elimination, forming a ring. http://organicreactions.org/index.php/Wacker_oxidation https://orcid.org/0000-0001-5985-7429 A cyclisation where an amino group acts as the nucleophile in a Wacker-Tsuji oxidation accompanied by beta-hydride elimination, forming a ring. aza-Wacker cyclization RXNO RXNO:0000648 aza-Wacker cyclisation RXNO:0000648 A cyclisation where an amino group acts as the nucleophile in a Wacker-Tsuji oxidation accompanied by beta-hydride elimination, forming a ring. http://organicreactions.org/index.php/Wacker_oxidation https://orcid.org/0000-0001-5985-7429 A cleaving reaction where an olefin is dihydroxylated with osmium tetroxide and undergoes a Malaprade reaction to yield two aldehydes, two ketones, or an aldehyde and a ketone. https://www.wikidata.org/wiki/Q6521154 RXNO RXNO:0000649 Lemieux-Johnson oxidation RXNO:0000649 A cleaving reaction where an olefin is dihydroxylated with osmium tetroxide and undergoes a Malaprade reaction to yield two aldehydes, two ketones, or an aldehyde and a ketone. https://doi.org/10.1021/jo01110a606 https://orcid.org/0000-0001-5985-7429 A cleaving reaction of a 1,2-diol using periodic acid to give the corresponding carbonyl compounds. https://www.wikidata.org/wiki/Q10851620 RXNO RXNO:0000650 Malaprade reaction RXNO:0000650 A cleaving reaction of a 1,2-diol using periodic acid to give the corresponding carbonyl compounds. https://doi.org/10.1039/C8CC09208G https://orcid.org/0000-0001-5985-7429 The oxidation of a 1,2-glycol with Fenton's reagent (hydrogen peroxide and iron salts) to give an alpha-hydroxy aldehyde. RXNO RXNO:0000651 Fenton 1,2-glycol oxidation RXNO:0000651 The oxidation of a 1,2-glycol with Fenton's reagent (hydrogen peroxide and iron salts) to give an alpha-hydroxy aldehyde. rsc:db The oxidation of an alpha-hydroxy carboxylic acid with Fenton's reagent to give an alpha-keto carboxylic acid. RXNO RXNO:0000652 Fenton alpha-hydroxy carboxylic acid oxidation RXNO:0000652 The oxidation of an alpha-hydroxy carboxylic acid with Fenton's reagent to give an alpha-keto carboxylic acid. RSC:db The reaction of the components of Fenton's reagent, viz. reduction of hydrogen peroxide by Fe(II) , producing an hydroxyl radical. RXNO RXNO:0000653 Fenton hydrogen peroxide reduction RXNO:0000653 The reaction of the components of Fenton's reagent, viz. reduction of hydrogen peroxide by Fe(II) , producing an hydroxyl radical. RSC:db The Mukaiyama hydration is an organic reaction involving formal addition of an equivalent of water across an alkene by the action of catalytic bis(acetylacetonato)cobalt(II) complex, phenylsilane and atmospheric oxygen. 2021-05-11T07:40:36Z RXNO RXNO:0000654 Mukaiyama hydration RXNO:0000654 The Mukaiyama hydration is an organic reaction involving formal addition of an equivalent of water across an alkene by the action of catalytic bis(acetylacetonato)cobalt(II) complex, phenylsilane and atmospheric oxygen. https://en.wikipedia.org/wiki/Mukaiyama_hydration A reaction between an alkyne and a carbonyl group under basic conditions in which a terminal alkyne serves as the CH-acidic moiety. When the carbonyl is an aldehyde, the 'Favorskii rearrangement' (RXNO:0000385) takes place and leads to an enone. 2021-05-17T08:17:36Z RXNO Faworski-Babayan reaction RXNO:0000655 Favorskii reaction RXNO:0000655 A reaction between an alkyne and a carbonyl group under basic conditions in which a terminal alkyne serves as the CH-acidic moiety. When the carbonyl is an aldehyde, the 'Favorskii rearrangement' (RXNO:0000385) takes place and leads to an enone. https://en.wikipedia.org/wiki/Favorskii_reaction Reductions with diimide are a chemical reactions that convert unsaturated organic compounds to reduced alkane products. In the process, diimide is oxidized to dinitrogen. 2021-05-17T08:35:08Z RXNO RXNO:0000656 Diimide reduction RXNO:0000656 Reductions with diimide are a chemical reactions that convert unsaturated organic compounds to reduced alkane products. In the process, diimide is oxidized to dinitrogen. https://en.wikipedia.org/wiki/Reductions_with_diimide A protection reaction where the reactive centre is a carbonyl oxygen. 2021-05-17T09:33:23Z RXNO RXNO:0000657 carbonyl group protection RXNO:0000657 The acid-catalyzed formation of an acetal (or ketal) to protect a carbonyl group by nucleophilic addition of an alcohol to an aldehyde (or ketone) with the elimination of water. 2021-05-17T09:38:59Z RXNO acetalisation acetalization RXNO:0000658 acetal protection RXNO:0000658 The acid-catalyzed formation of an acetal (or ketal) to protect a carbonyl group by nucleophilic addition of an alcohol to an aldehyde (or ketone) with the elimination of water. https://en.wikipedia.org/wiki/Acetal A chemical reaction that allows the generation of boronates from vinyl or aryl halides with the cross-coupling of bis(pinacolato)diboron under basic conditions. 2021-11-04T10:48:44Z Miyaura boration Miyaura borylation reaction RXNO RXNO:0000659 Miyaura borylation RXNO:0000659 A chemical reaction that allows the generation of boronates from vinyl or aryl halides with the cross-coupling of bis(pinacolato)diboron under basic conditions. https://www.organic-chemistry.org/namedreactions/miyaura-borylation-reaction.shtm https://www.rsc.org/Merck-Index/reaction/r288/miyaura%20boration?q=unauthorize A chemical reaction for the stereoselective synthesis of an olefin from a 1,2-diol. 2021-11-04T11:03:16Z RXNO Corey-Winter fragmentation Corey-Winter olefination Corey–Winter olefin synthesis RXNO:0000660 Corey-Winter elimination RXNO:0000660 A chemical reaction for the stereoselective synthesis of an olefin from a 1,2-diol. https://en.wikipedia.org/wiki/Corey%E2%80%93Winter_olefin_synthesis https://www.organic-chemistry.org/namedreactions/corey-winter-olefin-synthesis.shtm The Tsuji-Wilkinson decarbonylation reaction is a method for the decarbonylation of aldehydes and some acyl chlorides. 2021-11-04T12:09:26Z RXNO RXNO:0000661 Tsuji-Wilkinson decarbonylation RXNO:0000661 The Tsuji-Wilkinson decarbonylation reaction is a method for the decarbonylation of aldehydes and some acyl chlorides. https://dbpedia.org/page/Tsuji%E2%80%93Wilkinson_decarbonylation_reaction Although decarbonylation can be effected by several transition metal complexes, Wilkinson's catalyst has proven the most effective. A chemical reaction in which ketones are synthesized from formaldehyde or other aldehydes, involving a temporary repolarization of a carbonyl group. 2021-11-05T07:51:22Z RXNO Corey-Seebach Umpolung Seebach Umpolung RXNO:0000662 Corey-Seebach reaction RXNO:0000662 A chemical reaction in which ketones are synthesized from formaldehyde or other aldehydes, involving a temporary repolarization of a carbonyl group. https://en.wikipedia.org/wiki/Corey-Seebach_reaction https://www.organic-chemistry.org/namedreactions/corey-seebach-reaction.shtm Usually, the aldehyde is first reacted with propane-1,3-dithiol to form a 1,3-dithiane, which then reacts with an electrophile after deprotonation with n-butyllithium. Nitroxide exchange reactions are based on thermal C–O bond homolysis of alkoxyamines, which leads to transient carbon-centred radicals and persistent nitroxide radicals. Usually these carbon centred radicals are quickly trapped by the nitroxide radicals and reform the alkoxyamines. 2021-11-12T08:28:13Z RXNO RXNO:0000663 IUPAC does not recommend the use of the often synonymously used terms "nitroxyl radicals" or "nitroxides" for the class of "aminoxyl radicals". nitroxide exchange reaction RXNO:0000663 Nitroxide exchange reactions are based on thermal C–O bond homolysis of alkoxyamines, which leads to transient carbon-centred radicals and persistent nitroxide radicals. Usually these carbon centred radicals are quickly trapped by the nitroxide radicals and reform the alkoxyamines. https://doi.org/10.1039/C6RA06510D IUPAC does not recommend the use of the often synonymously used terms "nitroxyl radicals" or "nitroxides" for the class of "aminoxyl radicals". https://doi.org/10.1351/goldbook.A00285 https://doi.org/10.1351/goldbook.N04171 The conversion of pyran or pyrone (pyranone) derivatives to the corresponding pyridine derivative. 2021-11-12T09:25:38Z RXNO RXNO:0000664 Baeyer pyridine synthesis RXNO:0000664 The conversion of pyran or pyrone (pyranone) derivatives to the corresponding pyridine derivative. https://doi.org/10.1021/cr60130a004 Oxidation of primary and secondary alcohols via their alkoxysulfonium salts. Upon the addition of base, the salt rearranges intramolecularly to aldehydes and ketones, respectively. 2021-11-15T08:58:15Z RXNO Corey-Kim reaction RXNO:0000665 Corey-Kim oxidation RXNO:0000665 Oxidation of primary and secondary alcohols via their alkoxysulfonium salts. Upon the addition of base, the salt rearranges intramolecularly to aldehydes and ketones, respectively. https://www.rsc.org/Merck-Index/reaction/r90/corey-kim%20oxidation Oxidation of primary and secondary alcohols to aldehydes and ketones, respectively, through the use of pyridinium chlorochromate (PCC). 2021-11-15T09:09:31Z RXNO PCC oxidation RXNO:0000666 Corey-Suggs oxidation RXNO:0000666 Oxidation of primary and secondary alcohols to aldehydes and ketones, respectively, through the use of pyridinium chlorochromate (PCC). https://www.rsc.org/Merck-Index/reaction/r92/corey-suggs%20pcc%20oxidation Oxidation of primary and secondary alcohols to aldehydes and ketones, respectively, through the use of pyridinium dichromate (PDC). 2021-11-15T09:20:03Z RXNO PDC oxidation RXNO:0000667 Corey-Schmidt oxidation RXNO:0000667 Oxidation of primary and secondary alcohols to aldehydes and ketones, respectively, through the use of pyridinium dichromate (PDC). https://second.wiki/wiki/corey-schmidt-oxidation A particularly mild oxidation method in which, for example, dimethyl sulfoxide and acetic anhydride can be used as oxidizing agents to selectively produce aldehydes from primary alcohols without further oxidation to carboxylic acids. Analogously, secondary alcohols can be oxidized to form ketones. 2021-11-15T09:30:47Z RXNO RXNO:0000668 Albright-Goldman oxidation RXNO:0000668 A particularly mild oxidation method in which, for example, dimethyl sulfoxide and acetic anhydride can be used as oxidizing agents to selectively produce aldehydes from primary alcohols without further oxidation to carboxylic acids. Analogously, secondary alcohols can be oxidized to form ketones. https://en.wikipedia.org/wiki/Albright-Goldman_oxidation The Rubottom oxidation is a useful, high-yielding chemical reaction between silyl enol ethers and peroxy acids to give the corresponding α-hydroxy carbonyl product. 2021-11-15T09:44:42Z RXNO Rubottom reaction RXNO:0000669 Rubottom oxidation RXNO:0000669 The Rubottom oxidation is a useful, high-yielding chemical reaction between silyl enol ethers and peroxy acids to give the corresponding α-hydroxy carbonyl product. https://en.wikipedia.org/wiki/Rubottom_oxidation A three-component reaction (3CR) of a heterocyclic amidine, an aldehyde, and an isocyanide, resulting in a cyclic compound with imidazo[1,2-a] heterocycle as the core structure. 2021-12-03T09:13:40Z GBB reaction GBB‐3CR reaction RXNO RXNO:0000670 Groebke-Blackburn-Bienaymé reaction RXNO:0000670 A three-component reaction (3CR) of a heterocyclic amidine, an aldehyde, and an isocyanide, resulting in a cyclic compound with imidazo[1,2-a] heterocycle as the core structure. https://doi.org/10.1002/ejoc.201901124 The preparation of oxindole/indolin-2-one from 2-nitrophenylacetic acid by reduction of the nitro group and subsequent dehydration. 2021-12-03T14:20:07Z RXNO Baeyer indolinone synthesis RXNO:0000671 Baeyer oxindole synthesis RXNO:0000671 The preparation of oxindole/indolin-2-one from 2-nitrophenylacetic acid by reduction of the nitro group and subsequent dehydration. https://doi.org/10.1021/cr60118a003 Condensation of a formamide acetal with a derivative of o-nitrotoluene to yield an enamine intermediate that subsequently undergoes reductive cyclization to give the corresponding indole. 2021-12-03T14:45:01Z Batcho-Leimgruber indole synthesis RXNO RXNO:0000672 Leimgruber-Batcho indole synthesis RXNO:0000672 Condensation of a formamide acetal with a derivative of o-nitrotoluene to yield an enamine intermediate that subsequently undergoes reductive cyclization to give the corresponding indole. https://www.rsc.org/Merck-Index/reaction/r253/leimgruber-batcho%20indole%20synthesis Oxidation of alcohols to the corresponding carbonyl product using 2-iodoxybenzoic acid (IBX) as oxidizing agent. 2021-11-15T11:24:35Z RXNO RXNO:0000673 IBX oxidation and Dess-Martin oxidation are alcohol oxidation by hypervalent iodine reagents. The Dess-Martin periodinane used for oxidation in the Dess-Martin oxidation is prepared by reacting IBX with acetic anhydride in DMSO. IBX oxidation RXNO:0000673 Oxidation of alcohols to the corresponding carbonyl product using 2-iodoxybenzoic acid (IBX) as oxidizing agent. https://doi.org/10.1021/ol026427n A chemical reaction in which a carboxylic acid (or its salt) reacts with an organic (alkyl or aryl) halide to form a new carbon-carbon bond with concomitant loss of CO2. In addition, the reaction requires a metal catalyst, a base and an oxidizing agent. 2021-12-06T08:44:51Z RXNO RXNO:0000674 decarboxylative cross-coupling RXNO:0000674 A chemical reaction in which a carboxylic acid (or its salt) reacts with an organic (alkyl or aryl) halide to form a new carbon-carbon bond with concomitant loss of CO2. In addition, the reaction requires a metal catalyst, a base and an oxidizing agent. https://en.wikipedia.org/wiki/Decarboxylative_cross-coupling A carbon-carbon coupling reaction between an arene and an alkene to give a substituted arene. The reaction is catalysed by a Lewis acid. 2021-12-06T11:08:37Z RXNO RXNO:0000675 Balsohn alkylation RXNO:0000675 A carbon-carbon coupling reaction between an arene and an alkene to give a substituted arene. The reaction is catalysed by a Lewis acid. https://second.wiki/wiki/balsohn-alkylierung A three-component condensation reaction in which primary or secondary amines react with a carbonyl compound (aldehyde or ketone) and a dialkyl phosphonate (also called dialkyl phosphite) to form an alpha-aminophosphonate. 2021-12-13T11:39:08Z RXNO phospha-Mannich reaction RXNO:0000676 Kabachnik-Fields reaction RXNO:0000676 A three-component condensation reaction in which primary or secondary amines react with a carbonyl compound (aldehyde or ketone) and a dialkyl phosphonate (also called dialkyl phosphite) to form an alpha-aminophosphonate. https://doi.org/10.3390/molecules171112821 A polymerisation reaction in which phenol and formaldehyde react together in a chain reaction to form a phenol formaldehyde resin (also infrequently called phenoplast). 2021-12-13T12:52:17Z RXNO RXNO:0000677 Baekeland-Manasse-Lederer reaction RXNO:0000677 A polymerisation reaction in which phenol and formaldehyde react together in a chain reaction to form a phenol formaldehyde resin (also infrequently called phenoplast). https://doi.org/10.1021/ie50003a004 The rearrangement of an alpha-haloketone into an ester with a tertiary alpha-carbon atom by intramolecular migration of an alkyl or aryl group. 2021-12-14T08:15:45Z RXNO RXNO:0000678 Aston-Greenburg rearrangement RXNO:0000678 The rearrangement of an alpha-haloketone into an ester with a tertiary alpha-carbon atom by intramolecular migration of an alkyl or aryl group. https://doi.org/10.1021/ja01867a003 The rearrangement/migration of alkyl groups in polyalkylbenzenes or polynuclear aromatic compounds in the presence of anhydrous aluminum chloride or the mixture of protonic acid and Lewis acid. 2021-12-14T08:45:33Z RXNO RXNO:0000679 Baddeley isomerization RXNO:0000679 The rearrangement/migration of alkyl groups in polyalkylbenzenes or polynuclear aromatic compounds in the presence of anhydrous aluminum chloride or the mixture of protonic acid and Lewis acid. https://doi.org/10.1002/9780470638859.conrr030 The reduction of a thioester to an aldehyde by a silyl hydride in the presence of catalytic amounts of palladium. 2021-12-14T09:43:52Z RXNO RXNO:0000680 Fukuyama reduction RXNO:0000680 The reduction of a thioester to an aldehyde by a silyl hydride in the presence of catalytic amounts of palladium. https://en.wikipedia.org/wiki/Fukuyama_reduction https://www.rsc.org/Merck-Index/reaction/r163/fukuyama%20reduction A three component cyclization of an aromatic or vinylic alkoxy pentacarbonyl chromium carbene complex, an alkyne and carbon monoxide to give a Cr(CO)3 coordinated phenol. 2021-12-14T10:45:04Z RXNO Doetz reaction Wulff-Dötz reaction benzannulation reaction of Fischer carbene complexes RXNO:0000681 Dötz reaction RXNO:0000681 A three component cyclization of an aromatic or vinylic alkoxy pentacarbonyl chromium carbene complex, an alkyne and carbon monoxide to give a Cr(CO)3 coordinated phenol. https://en.wikipedia.org/wiki/Wulff%E2%80%93D%C3%B6tz_reaction https://www.rsc.org/Merck-Index/reaction/r116/d%C3%B6tz%20reaction The formation of a substituted cyclopropanol by reaction of a carboxylic ester with a Grignard reagent (carrying a hydrogen atom in the beta-position) in the presence of a titanium(IV) alkoxide as catalyst. A modified cyclopropanol product can be generated by addition of a terminal alkene as a further reactant. 2021-12-15T09:10:05Z RXNO RXNO:0000682 The dialkyldialkoxytitanium reagent, which actually reacts with the carboxylic ester, is generated in situ from the Grignard reagent and the titanium(IV) alkoxide. Kulinkovich reaction RXNO:0000682 The formation of a substituted cyclopropanol by reaction of a carboxylic ester with a Grignard reagent (carrying a hydrogen atom in the beta-position) in the presence of a titanium(IV) alkoxide as catalyst. A modified cyclopropanol product can be generated by addition of a terminal alkene as a further reactant. https://en.wikipedia.org/wiki/Kulinkovich_reaction https://www.rsc.org/Merck-Index/reaction/r247/kulinkovich%20reaction The formation of a substituted cyclopropylamine by reaction of an amide with a Grignard reagent (carrying a hydrogen atom in the beta-position) in the presence of a titanium(IV) alkoxide as catalyst. 2021-12-15T10:14:52Z RXNO RXNO:0000683 The Kulinkovich-de Meijere reaction is a modification of the Kulinkovich reaction (i.e., the reaction of an amide instead of a carboxylic ester under Kulinkovich conditions). Kulinkovich-de Meijere reaction RXNO:0000683 The formation of a substituted cyclopropylamine by reaction of an amide with a Grignard reagent (carrying a hydrogen atom in the beta-position) in the presence of a titanium(IV) alkoxide as catalyst. https://en.wikipedia.org/wiki/Kulinkovich_reaction https://www.rsc.org/Merck-Index/reaction/r247/kulinkovich%20reaction The formation of a substituted primary cyclopropylamine by reaction of a nitrile with a Grignard reagent (carrying a hydrogen atom in the beta-position) in the presence of a titanium(IV) alkoxide as catalyst. 2021-12-15T10:47:43Z RXNO RXNO:0000684 The Kulinkovich-Szymoniak reaction is a modification of the Kulinkovich reaction (i.e., the reaction of a nitrile instead of a carboxylic ester under Kulinkovich conditions). Kulinkovich-Szymoniak reaction RXNO:0000684 The formation of a substituted primary cyclopropylamine by reaction of a nitrile with a Grignard reagent (carrying a hydrogen atom in the beta-position) in the presence of a titanium(IV) alkoxide as catalyst. https://en.wikipedia.org/wiki/Kulinkovich_reaction https://www.rsc.org/Merck-Index/reaction/r247/kulinkovich%20reaction Chiral (salen)manganese(III)-catalyzed asymmetric epoxidation of alkenes. In addition to the catalyst, stoichiometric amounts of an oxidant (e.g. sodium hypochlorite) are required. 2021-12-16T08:34:02Z RXNO Jacobsen-Katsuki epoxidation RXNO:0000686 Jacobsen epoxidation RXNO:0000686 Chiral (salen)manganese(III)-catalyzed asymmetric epoxidation of alkenes. In addition to the catalyst, stoichiometric amounts of an oxidant (e.g. sodium hypochlorite) are required. https://en.wikipedia.org/wiki/Jacobsen_epoxidation https://www.rsc.org/Merck-Index/reaction/r218/jacobsen%20epoxidation Organocatalytic enantioselective epoxidation of trans- and tri-substituted olefins using a fructose derived chiral ketone catalyst and potassium peroxomonosulfate or H2O2 as an oxidant. 2021-12-16T08:57:48Z RXNO RXNO:0000687 Shi epoxidation RXNO:0000687 Organocatalytic enantioselective epoxidation of trans- and tri-substituted olefins using a fructose derived chiral ketone catalyst and potassium peroxomonosulfate or H2O2 as an oxidant. https://www.rsc.org/Merck-Index/reaction/r399/shi%20epoxidation A multicomponent reaction (A-4CR) in which 3-thiazolines (2,5-dihydro-1,3-thiazoles) or mixtures of several 3-thiazolines are synthesized from elemental sulfur, an alpha-substitutable ketone or aldehyde, another carbonyl component and ammonia. 2021-12-16T09:29:30Z RXNO Asinger thiazoline synthesis Asinger-4 component reaction (A-4CR) RXNO:0000688 Asinger reaction RXNO:0000688 A multicomponent reaction (A-4CR) in which 3-thiazolines (2,5-dihydro-1,3-thiazoles) or mixtures of several 3-thiazolines are synthesized from elemental sulfur, an alpha-substitutable ketone or aldehyde, another carbonyl component and ammonia. https://doi.org/10.1002/cmdc.202100086 https://en.wikipedia.org/wiki/Asinger_reaction Cleavage of methyl ketones (i.e. oxidative demethylation) with halogens (or hypohalites) in the presence of a base to give a carboxylic acid and haloform (trihalomethane). 2021-12-16T11:10:42Z RXNO Einhorn reaction Lieben reaction RXNO:0000689 haloform reaction RXNO:0000689 Cleavage of methyl ketones (i.e. oxidative demethylation) with halogens (or hypohalites) in the presence of a base to give a carboxylic acid and haloform (trihalomethane). https://en.wikipedia.org/wiki/Haloform_reaction https://www.rsc.org/Merck-Index/reaction/r257/lieben%20iodoform%20reaction The conversion of dialkyl phosphites (dialkyl phosphonates) to dialkyl chlorophosphates using tetrachloromethane and a base (usually a primary, secondary or tertiary amine). 2021-12-16T12:05:47Z RXNO AT reaction RXNO:0000690 Since the dialkyl chlorophosphates formed are often too reactive to be isolated, conversion to the corresponding phosphate or phosphoramidate occurs in the presence of a suitable nucleophile (e.g., alcohol or amine) after the actual Atherton-Todd reaction. Atherton-Todd reaction RXNO:0000690 The conversion of dialkyl phosphites (dialkyl phosphonates) to dialkyl chlorophosphates using tetrachloromethane and a base (usually a primary, secondary or tertiary amine). https://doi.org/10.3762/bjoc.10.117 https://en.wikipedia.org/wiki/Atherton%E2%80%93Todd_reaction Synthesis of diarylmethane derivatives using an aldehyde and an aromatic compound at low temperature in an acidic medium. 2021-12-16T12:54:23Z RXNO RXNO:0000691 A Friedel-Crafts type reaction proceeding via electrophilic aromatic substitution. Baeyer diarylmethane synthesis RXNO:0000691 Synthesis of diarylmethane derivatives using an aldehyde and an aromatic compound at low temperature in an acidic medium. https://doi.org/10.1016/B978-0-08-096630-4.00412-8 A hydroxyl group deprotection in which an silyl ether group is transformed into a hydroxy group. 2021-12-16T13:23:35Z RXNO RXNO:0000692 silyl deprotection RXNO:0000692 releases/2021-12-16 RXNO BFO:0000055 realizes RXNO BFO:0000057 has_participant RXNO BFO:0000077 has participant beginning to exist RXNO BFO:0000078 has participant ceasing to exist RXNO BFO:0000162 has disposition at all times This relation obtains between a planned process and a objective specification when the criteria specified in the objective specification are met at the end of the planned process. RXNO OBI:0000417 achieves_planned_objective This relation obtains between a planned process and a objective specification when the criteria specified in the objective specification are met at the end of the planned process. obi:AR obi:BP obi:PPPBbranch The notion here is that a given reaction is meant to 'protect' a given group from reacting in a subsequent process and can be 'deprotected' later. RXNO RXNO:0000416 can we chain 'has specified reactant' (RXNO:0000424) and has_part ? protects The notion here is that a given reaction is meant to 'protect' a given group from reacting in a subsequent process and can be 'deprotected' later. https://orcid.org/0000-0001-5985-7429 If a reaction R deprotects a group G, then G is in the product where it wasn't in the reactant. RXNO RXNO:0000417 can we chain 'has specified product' (RXNO:0000423) and has_part ? deprotects If a reaction R deprotects a group G, then G is in the product where it wasn't in the reactant. https://orcid.org/0000-0001-5985-7429 A relation between a planned reaction step and a molecular entity participating in that process. The creation of the molecular entity during the process is explicitly specified in the objective specification which the planned reaction step realizes the concretization of. RXNO RXNO:0000423 The difference between this and OBI's has_specified_output is that it is necessary that the participant starts to exist during the process. has specified product A relation between a planned reaction step and a molecular entity participating in that process. The creation of the molecular entity during the process is explicitly specified in the objective specification which the planned reaction step realizes the concretization of. https://orcid.org/0000-0001-5985-7429 A relation between a planned reaction step and a molecular entity participating in that process that is not created during the process. The destruction of the molecular entity during the process is explicitly specified in the plan specification which the process realizes the concretization of. RXNO RXNO:0000424 The difference between this and OBI's has_specified_input is that it is necessary that the reactant ceases to exist during the process. has specified reactant A relation between a planned reaction step and a molecular entity participating in that process that is not created during the process. The destruction of the molecular entity during the process is explicitly specified in the plan specification which the process realizes the concretization of. https://orcid.org/0000-0001-5985-7429 A relation between a planned reaction step and a molecular entity participating in that process that has_role catalyst ((CHEBI:35223). RXNO RXNO:0000425 has_catalyst A relation between a planned reaction step and a molecular entity participating in that process that has_role catalyst ((CHEBI:35223). https://orcid.org/0000-0001-5985-7429 A relation between a planned reaction step and a molecular entity participating in that process. The creation and subsequent destruction of the molecular entity during the process are explicitly specified in the plan specification which the process realizes the concretization of. RXNO RXNO:0000469 has_intermediate A relation between a planned reaction step and a molecular entity participating in that process. The creation and subsequent destruction of the molecular entity during the process are explicitly specified in the plan specification which the process realizes the concretization of. https://orcid.org/0000-0001-5985-7429 RXNO is the name reaction ontology. It contains more than 500 classes representing organic reactions such as the Diels–Alder cyclization. RXNO 16:12:2021 15:55 RXNO 1.2 RXNO has_part has_part