Electrophilic cleavage of cyclopropanes. Acetolysis of alkylcyclopropanes

KB Wiberg, SR Kass

Index: Wiberg, Kenneth B.; Kass, Steven R. Journal of the American Chemical Society, 1985 , vol. 107, # 4 p. 988 - 995

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Citation Number: 47

Abstract

Abstract: The solvent kinetic hydrogen isotope effect showed that proton transfer is at least partially rate determining for the acetolysis of cyclopropanes which span a range of 1Olo in reactivity. The energies and structures of protonated cyclobutanes were calculated and provide an explanation for the large difference in reactivity between cyclopropanes and cyclobutanes despite their similarity in enthalpies of reaction. The rates and products of ...