Studies on Phenazines. XIII.

On the Mechanism of Wohl-Aue Reaction

Abstract

The mechanism of the Wohl-Aue reaction was assumed as the nucleophilic substitution of aniline into the ortho-position of nitrobenzene to form o-nitrodiphenylamine, which undergoes reduction and ring cleavage to form phenazine by the action of excess of aniline as the oxygen-acceptor. Nitrobenzene is oxidized to o-nitrophenol by the action of alkali but this is thought to be a side reaction.