Oxidation of N-Alkylhydroxylamines. IV. Anodic Oxidation of N-Alkylhydroxylamines

Abstract

The anodic oxidation of N-monoalkyl and N, N-dialkylhydroxylamines in acetonitrile was studied. These hydroxylamines showed two anodic waves at glassy-carbon electrode. Controlled potential electrolysis of the hydroxylamines at the first wave consumed two electrons per molecule oxidized. N-Alkylhydroxylamines and N, N-dimethylhydroxylamine gave the corresponding nitroso compounds and a nitrone, MeN(O)=CH₂, respectively, while N, N-di-t-butylhydroxylamine gave t-nitrosobutane, t-butanol and isobutene. In the anodic oxidation the peak potentials were linearly related with the second order rate constants for oxidation of the hydroxylamines with DPPH, except in the case of N, N-di-t-butylhydroxylamine and di-t-butylnitroxide.