Stereoselective Synthesis of (Z)-1,2-Bis(arylsulfanyl)ethenes with Calcium Carbide as a Solid Alkyne Source

Abstract

AbstractA concise stereoselective synthesis of (Z)-1,2-bis(arylsulfanyl)ethenes by the reaction of arylsulfonyl chlorides with calcium carbide in the presence of cuprous iodide as a catalyst is described. The salient features of this protocol are its use of an inexpensive and easily handled solid alkyne source as a surrogate for flammable and explosive gaseous acetylene, its commercially available starting materials, its high stereoselectivity, and its simple workup procedures. The stereochemical structure of a selected product was determined by single-crystal X-ray diffraction. This method can be extended to a gram scale.