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willgerodt rearrangement wikipedia jump to content main menu main menu move to sidebar hide navigation main page contents current events random article about wikipedia contact us contribute help learn to edit community portal recent changes upload file special pages search search appearance donate create account log in personal tools donate create account log in contents move to sidebar hide top 1 willgerodt kindler reaction 2 references toggle the table of contents willgerodt rearrangement 7 languages deutsch español فارسی italiano 日本語 українська 中文 edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikimedia commons wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia chemical reaction willgerodt rearrangement named after conrad willgerodt reaction type rearrangement reaction identifiers rsc ontology id rxno 0000185 the willgerodt rearrangement or willgerodt reaction is an organic reaction converting an aryl alkyl ketone alkyne or alkene to the corresponding amide by reaction with ammonium polysulfide named after conrad willgerodt 1 2 3 4 the formation of the corresponding carboxylic acid is a side reaction resulting from hydrolysis of the amide when the alkyl group is an aliphatic chain n typically 0 to 5 multiple reactions take place with the amide group always ending up at the terminal end the net effect is thus migration of the carbonyl group to the end of the chain and oxidation general scheme for the willgerodt rearrangement an example with modified reagents sulfur concentrated ammonium hydroxide and pyridine is the conversion of acetophenone to 2 phenylacetamide and phenylacetic acid 5 the willgerodt rearrangement using acetophenone willgerodt kindler reaction edit willgerodt kindler reaction named after conrad willgerodt karl kindler reaction type rearrangement reaction identifiers organic chemistry portal willgerodt kindler reaction rsc ontology id rxno 0000186 the related willgerodt kindler reaction 6 takes place with elemental sulfur and an amine like morpholine the initial product is a thioamide for example that of acetophenone 7 which can again be hydrolyzed to the amide the reaction is named after karl kindler de the kindler modification of the willgerodt rearrangement a possible reaction mechanism for the kindler variation is depicted below 8 proposed mechanism for the willgerodt kindler reaction the first stage of the reaction is basic imine formation by the ketone group and the amine group of morpholine to give an enamine 1 this reacts as a nucleophile with electrophilic sulfur similar to an stork enamine alkylation reaction 2 verification needed the actual rearrangement reaction takes place when the amine group attacks the thiocarbonyl in a nucleophilic addition temporarily forming an aziridine 3 and the thioacetamide by tautomerization 4 this is hydrolysed to give the product amide 5 references edit willgerodt conrad 1887 ueber die einwirkung von gelbem schwefelammonium auf ketone und chinone berichte der deutschen chemischen gesellschaft 20 2 2467 2470 doi 10 1002 cber 18870200278 willgerodt conrad 1888 ueberführung von ketonen und aldehyden in säuren und säureamide mittelst gelben schwefelammoniums berichte der deutschen chemischen gesellschaft 21 1 534 536 doi 10 1002 cber 18870200278 carmack marvin f detar delos 1946 the willgerodt and kindler reactions iii amides from acetylenes and olefins studies relating to the reaction mechanisms journal of the american chemical society 68 10 2029 2033 doi 10 1021 ja01214a048 carmack marvin spielman m a 1946 the willgerodt reaction organic reactions 3 83 107 doi 10 1002 0471264180 or003 02 isbn 9780471005285 cite journal isbn date incompatibility help cs1 maint periodical has isbn link the willgerodt reaction ii a study of reaction conditions with acetophenone and other ketones delos f detar and marvin carmack j am chem soc 1946 68 10 2025 2029 doi 10 1021 ja01214a047 karl kindler 1923 studien über den mechanismus chemischer reaktionen erste abhandlung reduktion von amiden und oxydation von aminen liebigs annalen 431 1 187 230 doi 10 1002 jlac 19234310111 organic syntheses coll vol 9 p 99 1998 vol 74 p 257 1997 article name reactions and reagents in organic synthesis bradford p mundy michael g ellerd frank g jr favaloro 2005 isbn 0 471 22854 0 retrieved from https en wikipedia org w index php title willgerodt_rearrangement oldid 1345199363 categories rearrangement reactions name reactions hidden categories articles with short description short description matches wikidata cs1 errors isbn date cs1 maint periodical has isbn all pages needing factual verification wikipedia articles needing factual verification from may 2023 this page was last edited on 24 march 2026 at 21 23 utc page was rendered with parsoid text is available under the creative commons attribution sharealike 4 0 license additional terms may apply by using this site you agree to the terms of use and privacy policy wikipedia is a registered trademark of the wikimedia foundation inc a non profit organization privacy policy about wikipedia disclaimers contact wikipedia legal safety contacts code of conduct developers statistics cookie statement mobile view search search toggle the table of contents willgerodt rearrangement 7 languages add topic