Unusual reaction of azoxybenzenes with p-toluenesulfonic acid in acetic anhydride.
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概要
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Treatment of azoxybenzene with <I>p</I>-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.
- 公益社団法人 日本化学会の論文
著者
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Fujimori Ken
Department Of Anatomy School Of Medicine Faculty Of Pharmaceutical Sciences Tokushima University
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Shimao Ichiro
Department Of Applied Chemistry. Faculty Of Engineering Toyama University
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Oae Shigeru
Deparment of Applied Chemistry Faculty of Engineering Osaka City University
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