Abstract
When treated with arenesulfonyl chlorides, phenylhydroxylamines rearrange to o-arene-sulfonyloxyaniline derivatives. The rearrangement of N-benzoyl-phenylhydroxylamine, under the influence of p-nitrobenzenesulfonyl chloride, was studied in detail. The ortho:para ratio is greater than 50. The oxygen introduced into the aniline ring comes exclusively from the sulfonyl group on the sulfonyl chloride, as shown by O18 labeling. This demands a concerted. cyclic mechanism for the rearrangement of the intermediate N-benzoyl-N-(p-nitrobenzenesulfonyloxy) aniline.
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