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The Willgerodt rearrangement or Willgerodt reaction is an organic reaction converting an aryl alkyl ketone to the corresponding amide by reaction with ammonium polysulfide. 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.
Additional recommended knowledge
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 benzophenone  which can again be hydrolyzed to the amide.
The first stage of the reaction is basic imine formation by the ketone group and the amine group of morpholine to the enamine 4 which reacts in a conjugate addition (see Stork enamine alkylation for a related step) with sulfur to the sulfide 6. The actual rearrangement reaction takes place when the amine group attacks thiocarbonyl 7 in a nucleophilic addition temporarily forming an aziridine ring (8) and the amine group moving along the central C-C bond to 9 and after proton exchange to 10 and further on to the thioacetamide 11 by tautomerization.
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Willgerodt_rearrangement". A list of authors is available in Wikipedia.|