sodium Hypochlorite Reaction. II Degradation of N,N-Dimethylhydrazides

Abstract

The Hofmann degradation² involves treatment of carboxamides with an alkaline hypohalite solution, thereby engendering primary amines with one less carbon. It is well known that formation of N-haloamides constitutes the first step of the degradation. Removal of the remaining proton on the nitrogen atom triggers rearrangement with concomitant expulsion of the halide ion to afford isocyanates which are immediately hydrated and then decarboxylate in situ. Consequently, only unsubstituted amides are capable of undergoing the Hofmann reaction.