Rearrangements of diphenylamine derivatives. Part IV. Rearrangements of N-aroyldiphenylamines catalysed by aluminium chloride

Abstract

N-Benzoyl-, N-(p-toluoyl)-, and N-(p-chlorobenzoyl)-diphenylamine react with an excess of aluminium chloride at 140–180° to give the corresponding 4,4′-diaroyldiphenylamines and diphenylamine itself. N,4-Dibenzoyldiphenylamine gives only 4,4′-dibenzoyldiphenylamine under similar conditions, N-benzoyl-4-methyldiphenylamine gives only 4-methyldiphenylamine, and N-(p-nitrobenzoyl)diphenylamine does not yield tractable products. The reaction of diphenylamine with benzoyl chloride (2 mol. equiv.) and an excess of aluminium chloride at 140° yields N-benzoyldiphenylamine and 4,4′-dibenzoyldiphenylamine.