Bulletin of the Chemical Society of Japan p. 4061 - 4066 (1987)
Update date:2022-08-11
Topics:
Kozuka, Seizi
Tamura, Shoji
Ishibashi, Satoshi
Ohya, Sadamu
Tagaki, Waichiro
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.
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