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The Reaction of Azoxybenzene with Acetic Anhydride

1971; Oxford University Press; Volume: 44; Issue: 2 Linguagem: Inglês

10.1246/bcsj.44.442

1348-0634

Shigeru Ōae, Tetsuya Maeda, Seizi Kozuka,

Chemical Synthesis and Reactions

Abstract When azoxybenzene was allowed to react with equimolar amount of acetic anhydride, a mixture of azobenzene, acetanilide, and acetic acid was obtained along with such gaseous products as carbon dioxide, carbon monoxide and methane. In the reaction of azoxybenzene with an excess acetic anhydride, however, azobenzene was not isolated, and only acetanilide was obtained. Acetanilide and acetic acid were also obtained in the reaction of azobenzene with acetic anhydride. The results suggest the initial formation of azobenzene which is eventually converted to acetanilide in the subsequent reaction with an excess acetic anhydride. The formation of acetanilide was inhibited by the addition of such radical scavengers as iodine, hydroquinone, and nitrobenzene. A free radical mechanism is suggested for the reaction. Phenazine N-oxide also apparently undergoes similar reaction.