The hydrolysis of imidate salts. Stereoelectronic control in the cleavage of the hemiorthoamide tetrahedral intermediate

P Deslongchamps, S Dubé, C Lebreux…

Index: Deslongchamps,P. et al. Canadian Journal of Chemistry, 1975 , vol. 53, p. 2791 - 2807

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Citation Number: 42

Abstract

A new stereoelectronic theory for the cleavage of the tetrahedral intermediate (hemiorthoamide) in the hydrolysis of amides is presented. In this new theory, the precise conformation of the tetrahedral intermediate controls the nature of the hydrolysis products. It is postulated that the breakdown of the tetrahedral intermediate depends upon the orientation of the lone pair orbitals of the heteroatoms. Specific cleavage of a carbon- ...