Electrophilic cleavage of cyclopropanes. Acetolysis of bicyclo [2.1. 0] pentane and bicyclo [3.1. 0] hexane

KB Wiberg, SR Kass, KC Bishop III

文献索引：Wiberg,K.B.; Kass,S.R.; Bishop,K.C. Journal of the American Chemical Society, 1985 , vol. 107, p. 996

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被引用次数: 24

摘要

Abstract: The uncatalyzed acetolysis of bicyclo [2.1. O] pentane (1) leads to 47% cyclopentyl acetate and 53% cyclopentene. The reaction with p-toluenesulfonic acid in acetic acid is much more rapid and leads to 30% cyclopentyl acetate, 24% cyclopentyl tosylate, and 46% cyclopentene. The rate of acetolysis is decreased by a factor of 2.55 on going to AcOD as the solvent, indicating that proton transfer is at least partially rate determining. The ...