Relative Reactivities of Various Sulfides, Selenides and Halides Towards SH2 Attack by Tributyltin Radicals

Abstract

The order of reactivity towards SH2 attack by tributyltin radicals on various groups X in four different molecular environments (RCO2CH2X, RCH2OCH2X, XCH2CO2Et and RCH2X) has been found by competition experiments to be Br > PhSe > Cl > p-CNC6H4S > PhS > p-MeC6H4S > MeS . The mechanism of the reaction of chloromethyl phenyl sulfide with alkoxides is discussed.