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Willgerodt rearrangement
The Willgerodt rearrangement or Willgerodt reaction is an organic reaction converting an aryl alkyl ketone to the corresponding amide by reaction with ammonium polysulfide, named after Conrad Willgerodt.〔Willgerodt, Ber., 20, 2467 (1887) ; 21, 534 (1888) 〕〔Carmack, M.; Spielman, M. A. ''Org. React.'' 1946, ''3''.〕 The formation of the corresponding carboxylic acid is a side reaction. 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.
An example with modified reagents (sulfur, concentrated ammonium hydroxide and pyridine) is the conversion of acetophenone to 2-phenylacetamide and phenylacetic acid:〔''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. ()〕
==Willgerodt–Kindler reaction==
The related Willgerodt–Kindler reaction takes place with elemental sulfur and an amine like morpholine. The initial product is a thioacetamide for example that of acetophenone〔Organic Syntheses, Coll. Vol. 9, p.99 (1998); Vol. 74, p.257 (1997). ((Article ))〕 which can again be hydrolyzed to the amide. The reaction is named after Karl Kindler.
抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』
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