ICl-Mediated Functional Group Interconversion from Methyl Homopropargyl Ether to alpha-Iodo-gamma-chloroketone

An ICl-mediated highly chemo-and regioselective functional group interconversion from methyl homopropargyl ether to alpha-iodo-gamma-chloro-ketone is reported. Density functional theory (DFT)-calculated reaction coordinate and potential energy surface support the high chemo-selectivity observed for the formation of alpha-iodo-gamma-chloroketone over furan. The five -membered oxonium ring formation-ring opening mechanism is a potential template for the preparation of polyfunctionalized carbonyl compounds.