85034-13-5Relevant academic research and scientific papers
Chemistry of gem-Dihalocyclopropanes. XVII. Cyclopropylidene Incertion. Formation and Ring Opening of Bicyclobutan-2-olate
Nilsen, Nils O.,Skattebol, Lars,Sydnes, Leiv K.
, p. 587 - 592 (2007/10/02)
Reactions of gem-dibromocyclopropanemethanol derivatives 3a-3e with methyllithium lead to allenic alcohols 4a-4h and products which derive from ring opening of an intermediate bicyclobutan-2-olate (17).The latter is formed by insertion of the respective cyclopropylidene into a C-H bond.Evidence for 17 was obtained from deuterium labelling experiments.This ring opening generally occurs by a carbanion mechanism, but in the case of 3d the intermediate bicyclobutanolate rearranged to the acyclic aldehyde 10, apparently by a thermal mechanism.The secondary alcohols 3f-3h reacted with methyllithium to give the corresponding allenes exclusively, which was also the case with ethers 3i-3l derived from the primary alcohols.
