The limit of strain energy differential for intramolecular nucleophilic substitution via a sulfonyl-stabilised carbanion to give cyclopropane analogues in hydroxylic solvents is around 160 kJ mol–1; above this level, concerted, albeit unactivated, 1,2-elimination is preferred.
S. M. Jeffery, S. Niedoba and C. J. M. Stirling, J. Chem. Soc., Chem. Commun., 1992, 650 DOI: 10.1039/C39920000650
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