Journal of Organic Chemistry p. 3903 - 3908 (1988)
Update date:2022-08-16
Topics:
Novak, Michael
Bonham, Gayl A.
Mohler, Linda K.
Peet, Kristine M.
Although it has been widely assumed that N-hydroxy-N-aryl amides decompose in acidic solution by acid-catalyzed N-O bond heterolysis, we have found that the N-hydroxyacetanilides 1a-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 under the reaction conditions.Only the p-EtO- and p-MeO-substituted N-hydroxyacetanilides (1a and 1b) exhibit any sign of N-O bond heterolysis, and only as a minor component (ca. 7percent) of the overall hydrolysis.No change in mechanism could be found for 1d in H2SO4 solutions as concentrated as 9 M.The lack of reactivity of 1a-e to N-O bond heterolysis is largely due to unfavorable protonation of the OH group.Protonation of the carbonyl oxygen is favored over the hydroxyl oxygen by ca. 7 orders of magnitude.
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