Reaction of cyclic α-hydroxy epoxides with a strong base: A new 1,2-rearrangement, evidence for a carbenoid pathway

Article abstract of DOI:10.1021/ja00156a006

Several substituted five- and six-membered cyclic α,β-unsaturated ketones are readily available by treatment of the corresponding α-hydroxy epoxides with an organolithium reagent. The reaction involves a new carbenoid 1,2-alkyl rearrangement. Evidence for the carbenoid intermediate has been obtained by an intramolecular trapping of the highly reactive species.