Electrochemical transformation of N-nitrosodialkylamines into N-nitramines and .BETA.-ketonitrosamines.

Controlled potential electrolysis, based on the results of cyclic voltammetry, of simple dialkylnitrosamines such as N-nitrosodibutylamine and N-nitrosodicyclohexylamine in acetonitrile at a glassy carbon electrode resulted in the formation of the corresponding nitramines as the major products together with β-ketonitrosamines in which the carbonyl group is on the same side of the nitroso-oxygen atom. With N-nitrosopiperidine, one derived from a cyclic amine, N-nitropiperidine was formed similarly but the β-oxidized nitrosamine was not detected in the electrolysis solution. In deoxygenated acetonitrile, neither the nitramines nor the β-ketonitrosamines were obtained from the electrolysis.