Electrophilic cleavage of cyclopropanes. Acetolysis of bicyclic and tricyclic cyclopropanes

…, SR Kass, A De Meijere, KC Bishop III

Index: Wiberg, Kenneth B.; Kass, Steven R.; Meijere, Armin de; Bishop, K. C. Journal of the American Chemical Society, 1985 , vol. 107, # 4 p. 1003 - 1007

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Citation Number: 15

Abstract

Abstract: The acetolysis of a series of bicyclo [nl 0] alkanes and [nml] propellanes has been studied. The effect of ring strain, caused by changing ring size or introducing a trans-ring fusion, on the rate and products of the reaction has been examined. No correlation was found between rates of acetolysis and strain energy relief, but with the exception of [3.2. l] propellane, there is a rough correlation with ionization potentials. The degree of ...