29276-24-2Relevant academic research and scientific papers
Methylenecyclopropanes in elimination and addition reactions: Quantification of the effects of strain
Volta, Luca,Stirling, Charles J. M.
experimental part, p. 1508 - 1522 (2010/03/24)
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 60% of the excess enthalpy differential promotes the reactivity of the strained system.
The effect of strain on reactivity: Poor leaving groups increase strain-induced inhibition of alkene-forming elimination
Volta, Luca,Stirling, Charles J. M.
, p. 2481 - 2482 (2007/10/03)
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
