NUCLEOPHILIC RING OPENING OF EPOXIDES BY CARBANIONS; NOVEL FORMATION OF CYCLOPROPANE DERIVATIVES IN A NON-POLAR SOLVENT

Article abstract of DOI:10.1016/S0040-4020(01)92158-1

Nucleophilic ring-opening of epoxides 2(a-d) with carbanions of different steric requirements under refluxing benzene afforded a single stereoisomer of the cyclopropane derivatives 4.The same reaction under refluxing ethanol gave the normal products, i.e. the trans-lactones 6.Mechanism and high stereoselectivity observed in the novel cyclopropane formation, and regiospecific cleavage of the cyclopropane carboxylic acids (in 4) have also been discussed in detail.