Stereochemistry of iodofluorination of phenyl-substituted olefins with (difluoroiodo)methane
Abstract
(Difluoroiodo)methane reacts with substituted olefins, e.g. cis- and trans-stilbene, cis- and trans-β-alkylstyrenes, and indene, to form the corresponding iodo-fluorides. Iodofluorination proceeds with Markovnikov-type regioselectivity and is stereospecifically anti, forming the corresponding (±)-erythro- or (±)-threo-1-fluoro-2-iodo-1-phenylethanes.