Journal of the American Chemical Society

Influence of strain on chemical reactivity. Relative reactivity of torsionally distorted double bonds in MCPBA epoxidations

KJ Shea, JS Kim

Index: Shea, Kenneth J.; Kim, Jang-Seob Journal of the American Chemical Society, 1992 , vol. 114, # 8 p. 3044 - 3051

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Citation Number: 73

Abstract

Abstract: The second-order reaction rates were measured for the MCPBA epoxidation in CHQ, for a series of cyclic olefins including bridgehead olefins and tram-cycloalkenes. As expected, strained bridgehead alkenes and trans-cycloalkenes showed faster reaction rates than nonstrained cis-cycloalkenes. The MM-2 steric energies of alkenes, alkanes, and their corresponding epoxides were calculated to evaluate the strain energy released in each ...