Journal of the American Chemical Society

Absence of stereoelectronic control in hydrolysis of cyclic amidines

CL Perrin, O Nunez

文献索引：Perrin, Charles L.; Nunez, Oswaldo Journal of the American Chemical Society, 1986 , vol. 108, # 19 p. 5997 - 6003

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被引用次数: 38

摘要

Abstract: According to Deslongchamps' theory of stereoelectronic control, preferential cleavage of a tetrahedral intermediate occurs when there are two lone pairs antiperiplanar to the leaving group. For reasons presented (Perrin and Arrhenius, J. Am. Chem. Soc. 1982, 104, 2839), product studies of hydrolysis of cyclic amidines can test this theory, and initial results supported it. However, those results are ambiguous, owing to a mismatch of ...