The Mechanism of the Reaction of (Arylthio)trimethylgermanes with Benzyl Bromides Giving Aryl Benzyl Sulfides. A Kinetic Study

Article abstract of DOI:10.1246/bcsj.60.4061

A kinetic study has been conducted on the reaction of (arylthio)trimethylgermanes with benzyl bromides.The reaction was found to be second order and the rate was largely accelerated in polar solvents.Both ρ values due to substituents on arylthio and benzyl groups revealed nucleophilic attack of the sulfur atom on benzylic carbon atom as the reaction mechanism.Rates of the reactions of trimethyl(p-tolylthio)stannane with substituted benzyl chlorides were also examined to compare the substituent effects.Steric crowd around the sulfur atom has been found as an important factor to control the reaction mechanism.