Relative Reactivities of Various Sulfides, Selenides and Halides Towards S_H2 Attack by Tributyltin Radicals

Abstract

The order of reactivity towards S_H2 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.