I. Shimao, K. Fujimori, S. Ōae
May 1, 1982
Citations
0
Influential Citations
7
Citations
Journal
Bulletin of the Chemical Society of Japan
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 4-acetoxyphenyl tosylate and hydroquinone diacetate in high yields. These unique reactions involve C–N bond cleavage, and may proceed through a pathway involving formation of benzenediazonium ion as the key intermediate.