Electrochemical oxidation of amides of type Ph2CHCONHAr?

Organic & Biomolecular Chemistry Pub Date: 2012-02-28 DOI: 10.1039/C2OB06878H

Abstract

Anodic oxidation of N-aryl-2,2-diphenylacetamides in acetonitrile undergoes three types of bond-cleavage, one between the benzylic carbon and the carbonyl group, the second between a carbonyl and ‘N', and the third between the ‘N' atom and aryl group. The selectivity of the cleavage and nature of emerged products is highly dependent on the nature of substituent attached to the aryl group. For example, electron-withdrawing groups direct the benzyl–carbonyl bond-breaking whereas electron-donating substituents favor the N-aryl bond cleavage. The type of products obtained involve benzophenone, 2,2-diphenylacetamide, N-(diphenylmethylene)acetamide, N-(diphenylmethyl)acetamide, α-lactam (1-acetyl-3,3-diphenylaziridin-2-one, as a 1?:?1 complex with 2,4-dinitroaniline) and aniline derivatives.

Graphical abstract: Electrochemical oxidation of amides of type Ph2CHCONHAr
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