The electrolytic oxidation of anilines at a rotating platinum electrode in acetonitrile in the presence of pyridine involved a two electron change and formed azobenzenes. Evidence for the mechanism was the voltammetric behavior of hydrazobenzenes, p ‐phenylenediamine and 4,4'‐dimethoxyazobenzene and the formation of azobenzenes in macroscale oxidations. The behavior of anilines in the absence of pyridine was more complex since the amine acted as a base and formed a salt which was not easily oxidized. Exceptions were the weakly basic o ‐nitroaniline, p ‐nitroaniline, 2,4‐dinitroaniline and the reversible systems, o ‐phenylenediamine and p ‐phenylenediamine; two electrons were involved for these examples.
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Wawzonek et al. (1967) studied this question.