Hydrolysis of N-acetyl-p-benzoquinone imines: pH dependence of the partitioning of a tetrahedral intermediate

…, GA Bonham, JJ Mulero, M Pelecanou…

Index: Novak, Michael; Bonham, Gayl A.; Mulero, Julio J.; Pelecanou, Maria; Zemis, Joseph N.; et al. Journal of the American Chemical Society, 1989 , vol. 111, # 12 p. 4447 - 4456

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Citation Number: 15

Abstract

Abstract: The hydrolysis reactions of N-acetyl-p-benzoquinone imine, la, and its 33-and 2, 6- dimethyl analogues, 1 b and IC, in the pH range 0.3-10.5 are described. At pH< 6.0 the carbinolamide intermediates 2a-c can be detected by'H NMR, UV, and HPLC methods. The pH-dependent partitioning of 2a and 2c can be. monitored since the reversion of these intermediates to the protonated N-acylimines Sa and Sc leads to products of the conjugate ...