Acid-catalyzed hydrolysis of N-hydroxyacetanilides: amide hydrolysis versus nitrogen-oxygen bond heterolysis

M Novak, GA Bonham, LK Mohler…

Index: Novak, Michael; Bonham, Gayl A.; Mohler, Linda K.; Peet, Kristine M. Journal of Organic Chemistry, 1988 , vol. 53, # 17 p. 3903 - 3908

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Citation Number: 17

Abstract

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 ...

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