The cathodic cleavage of the nitrobenzoyl group from protected aliphatic amines in N,N-dimethylformamide

Abstract

The electrochemical reduction of aliphatic amines protected by the 4- and 3-nitrobenzoyl group in N,N-dimethylformamide was reported. The compounds are reduced in two cathodic steps. The first one at about -1 V vs. SCE occurs with the formation of the rather stable anion radicals, involving one electron transfer. The reduction to dianion occurs at potentials between -1.5 and -2.0 V vs. SCE by an ECE process and leads to cleavage of the CN bond in yields above 50%.