Acid-Catalyzed Solvolysis of N-Sulfonyl- and N-Acyl-O-arylhydroxylamines. Phenoxenium Ions

Article abstract of DOI:10.1021/ja00387a040

The acid-catalyzed reaction of N-acyl- and N-sulfonyl-O-arylhydroxylamines 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.