Non-catalyzed addition of secondary phosphine chalcogenides to divinyl chalcogenides under solvent-free conditions

Abstract

ABSTRACT Secondary phosphine chalcogenides, R2PX (R═(CH2)2Ph, Ph; X = S, Se), react with divinyl chalcogenides, (CH2═CH)2Y (Y = S, Se, Te), at the 2:1 molar ratio (80–82°C, 56–80 h) in the absence of both catalysts (initiators) and solvents to quantitatively afford the corresponding anti-Markovnikov diadducts. Even at the equimolar reactant ratio, the diadducts are the major products, though monoadducts are also formed. When Y = Te, vinylphosphine chalcogenides and metal Te are obtained, thus showing that divinyl telluride behaves as the vinylating agent.