The mechanism of the reaction of (arylthio)trimethylgermanes with benzyl bromides giving aryl benzyl sulfides. A kinetic study.

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概要

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• 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(<I>p</I>-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.

著者

• Tagaki Waichiro

  Department Of Bioapplied Chemistry Faculty Of Engineering Osaka City University

• Kozuka Seizi

  Department of Applied Chemistry, Faculty of Engineering, Osaka City University

• Ishibashi Satoshi

  Department of Applied Chemistry, Faculty of Engineering, Osaka City University

• Tamura Shoji

  Department of Applied Chemistry, Faculty of Engineering, Osaka City University

• Ohya Sadamu

  Department of Applied Chemistry, Faculty of Engineering, Osaka City University

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