The effect of strain on reactivity: poor leaving groups increase strain-induced inhibition of alkene-forming elimination

Abstract

Elimination to form a carbon–carbon double bond exocyclic to a cyclopropane ring is inhibited by factors which increase from 1.4 to 10^4.5 as the leaving group becomes poorer; strain induced in the transition structure can amount to some 50% of the enthalpy difference between strained and unstrained products.