Activation parameters for intramolecular nucleophilic substitution by carbanions—the insignificant effect of ring strain on cyclisation rates

F Benedetti, CJM Stirling

Index: Benedetti, Fabio; Stirling, Charles J. M. Journal of the Chemical Society, Chemical Communications, 1983 , # 22 p. 1374 - 1376

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Abstract

Activation parameters for the cyclisation of bis-sulphonyl-stabilised carbanions to bis-sulphonylcycloalkanes have been determined; cyclopropanes form nearly a million-fold faster than cyclobutanes and ring strain is a negligible factor in determining reactivity. ... The effect of structure on intramolecular nucleophilic substitu- tion has been studied systematically by several groups of workers for more than 50 years' but for carbocycle formation, however, few general conclusions have been ...