Journal of the American Chemical Society

Acid-Catalyzed Amide Hydrolysis Assisted by a Neighboring Amide Group

T Cohen, J Lipowitz

Index: Cohen,T.; Lipowitz,J. Journal of the American Chemical Society, 1964 , vol. 86, p. 5611 - 5616

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Citation Number: 16

Abstract

The acid-catalyzed hydrolysis of o-benzamido-N, I\ T-dicyclohexylbenzamide(I) in aqueous acetic acid containing sulfuric acid at 80" occurs at the N, N-dicyclohexylamide linkage and is at least lo4 times faster than the hydrolysis of the less sterically hindered model compound, N, N-dicyclohexylbenzamide (IV), under the same conditions. Several mechanisms are presented by which the o-benzamido group may participate in the ...