Phosphorus, Sulfur, and Silicon

Methylenecyclopropanes in Elimination and Addition Reactions: Quantification of the Effects of Strain

L Volta, CJM Stirling

Index: Volta, Luca; Stirling, Charles J. M. Phosphorus, Sulfur and Silicon and the Related Elements, 2009 , vol. 184, # 6 p. 1508 - 1522

Full Text: HTML

Citation Number: 2

Abstract

The effect of strain in 1, 2-elimination reactions that form methylenecyclopropanes has been evaluated for a series of leaving groups. The worse the leaving group, the greater is the inhibitory effect of strain build-up, which reaches 50% of the excess enthalpy differential for the poorest leaving group studied. In nucleophilic addition to an electrophilic methylenecyclopropane, comparison of strained and unstrained systems shows that about ...