Journal of the American Chemical Society

The timing of the proton-transfer process in carbonyl additions and related reactions. General-acid-catalyzed hydrolysis of imines and N-acylimines of benzophenone

JM Sayer, P Conlon

Index: Sayer, J. M.; Conlon, Patrick Journal of the American Chemical Society, 1980 , vol. 102, # 10 p. 3592 - 3600

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Citation Number: 52

Abstract

Abstract: Observed general-acid-catalyzed hydrolysis of benzophenone imines, Ph2C= NR, or the kinetically equivalent general-base-catalyzed hydrolysis of the conjugate acids Ph2C= N+ HR, corresponds mechanistically to general-base-catalyzed amine expulsion from the conjugate acid (T+) of the tetrahedral intermediate from water addition to Ph2C= NR. Brfnsted p values for this catalysis by carboxylate and cacodylate ions are 0.96 (for R ...