Acid-catalyzed solvolysis of N-sulfonyl-and N-acyl-O-arylhydroxylamines. Phenoxenium ions

Y Endo, K Shudo, T Okamoto

Index: Endo, Yasuyuki; Shudo, Koichi; Okamoto, Toshihiko Journal of the American Chemical Society, 1982 , vol. 104, # 23 p. 6393 - 6397

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Citation Number: 54

Abstract

Abstract: The acid-catalyzed reaction of N-acyl-and N-sulfonyl-Oarylhydroxylamines with benzene proceeded quite smoothly to give 2-and 4-hydroxybiphenyls, The results of product analysis, the orientation of the reaction, and the effects of substituents on the nitrogen atom and on the phenyl ring suggested a mechanism that involves a phenoxenium ion. The phenoxenium ion was trapped by benzene and other various nucleophiles.