The reactions of trimethyl(methylthio)- and trialkyl(arylthio)stannanes with alkyl halides

Add time:08/12/2019    Source:sciencedirect.com

The reaction of trimethyl(methylthio)stannane with methyl iodide was reinvestigated. Trimethylsulfonium iodide and iodotrimethylstannane were the products which were isolated. Trialkylhalostannanes and alkyl aryl sulfides were obtained in nearly quantitative yield by the reaction of trialkyl(arylthio)stannanes with alkyl halides. The rate of the reaction of the trialkyl(arylthio)stannanes with an alkyl iodide was much slower than that of trimethyl(methylthio)stannane under the same reaction conditions. Nucleophilic attack of the stannyl sulfur atom on the alkyl halide is suggested as the first step of the reaction.

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