A NEW TWO-CARBON OLEFIN HOMOLOGATION PROCEDURE THAT LEADS TO α-CHLOROENONES. AN EFFICIENT SYNTHESIS OF d,l-MUSCONE

Article abstract of DOI:10.1016/S0040-4020(01)80126-5

Dichloroketene-olefin cycloadducts, α,α-dichlorocyclobutanones, are easily converted to α-chloroenones through a 3-step (2-pot) sequence of reactions.The overall result is the insertion of a functionalized 2-carbon unit between the original olefinic carbons.The efficiency of the method is demonstrated by a high-yield synthesis of d,l-muscone.