Journal of the American Chemical Society

Hydrolysis of unsymmetrical acetamidines: leaving abilities and stereoelectronic effects

CL Perrin, O Nunez

Index: Perrin, Charles L.; Nunez, Oswaldo Journal of the American Chemical Society, 1987 , vol. 109, # 2 p. 522 - 527

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Citation Number: 22

Abstract

Abstract: Unsymmetrical acetamidines hydrolyze in alkaline D20 to a mixture of two acetamides and two amines. Product ratios from three N-methylated acetamidines and five N-alkyl-”-methylacetamidines were determined by NMR. The direction of cleavage is determined largely by the relative basicities of the two amines, rather than by the relative basicities of the two nitrogens in the tetrahedral intermediate. Steric repulsion in the ...