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

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Luca Volta and Charles J. M. Stirling


Abstract

Elimination to form a carbon–carbon double bond exocyclic to a cyclopropane ring is inhibited by factors which increase from 1.4 to 104.5 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.


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