Kinetic and stereochemical studies of the reaction of trialkyl(alkylthio and arylthio)stannanes with haloalkanes.
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概要
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A kinetic study has been conducted on the reaction of arylthio(trimethyl)stannane with haloalkanes giving halotrimethylstannane and alkyl aryl sulfide. The reaction has been found to obey second order kinetics. Substituent effects of the arylthio group, solvent effects, relative reactivities of the leaving halogens and steric effects of the haloalkanes have been investigated. Optically active (+)-1-methylheptyl bromide gives an inverted product <I>i.e.</I>, (−)-methyl 1-methylheptyl sulfide by the reaction with trimethyl(methylthio)stannane. A mechanism involving bimolecular nucleophilic attack of the sulfur atom on the haloalkane has been confirmed for the reaction.
- 公益社団法人 日本化学会の論文
著者
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Kozuka Seizi
Department of Applied Chemistry, Faculty of Engineering, Osaka City University
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Ohya Sadamu
Department of Applied Chemistry, Faculty of Engineering, Osaka City University
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