Bulletin of the Chemical Society of Japan

Unusual reaction of azoxybenzenes with p-toluenesulfonic acid in acetic anhydride.

I Shimao, K Fujimori, S Oae

Index: Shimao, Ichiro; Fujimori, Ken; Oae, Shigeru Bulletin of the Chemical Society of Japan, 1982 , vol. 55, # 5 p. 1538 - 1542

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Citation Number: 8

Abstract

Treatment of azoxybenzene with p-toluenesulfonic acid in acetic anhydride gave tosylates of 4-and 2-(phenylazo) phenols, and the corresponding acetates as by-product, besides azobenzene. However, a similar reaction of 4, 4′-difluoroazoxybenzene gave 2-tosyloxy-4, 4′-difluoroazobenzene as rearrangement product, besides 4-fluorophenyl tosylate and 4- fluorophenyl acetate. Meanwhile, the reaction of 4, 4′-diacetoxyazoxybenzene afforded ...