Reactions of 2-Halovinyl Aryl Sulfoxides with Organometallic Reagents

Article abstract of DOI:10.1021/jo00032a023

(E)- and (Z)-halovinyl aryl sulfoxides 1-4 were subjected to reactions with organocopper, organomagnesium, or organolithium reagents.The organometallic reagents gave different products: diorganocuprates led to formation of carbon-carbon bond, with production of alkenyl sulfoxides 5-10, whereas formation of carbon-sulfur bond and production of diaryl or aryl alkyl sulfoxides 11-13 were observed in the reaction with the other organometallics.Possible mechanisms for the two observed processes are briefly discussed.