Although it has been widely assumed that N-hydroxy-N-aryl amides decompose in acidic solution by acidcatalyzed N-0 bond heterolysis, we have found that the N- hydroxyacetanilides la-e largely decompose by the alternative amide hydrolysis pathway. The immediate products of hydrolysis, the hydroxylamines 2a-e, can be detected by direct or indirect methods, but these materials also decompose via the Bamberger rearrangement ...
