Electrolytic Oxidation of Aromatic Amines

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Abstract
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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