Stereochemistry of the C-S Bond Cleavage in cis-2-Methylcyclopentyl Phenyl Sulfoxide Radical Cation.

[摘要]：The TiO2 photocatalyzed oxidn. of cis-2-methylcyclopentyl Ph sulfoxide in the presence of Ag2SO4 in MeCN/H2O leads to the formation of 1-methylcyclopentanol, 1-methylcyclopentylacetamide, and Ph benzenethiosulfonate as the main reaction products. It is suggested that the C-S heterolysis in the radical cation is an unimol. process leading to an ion radical pair. Fast 1,2-hydride shift in the secondary carbocation leads to 1-methylcyclopentyl carbocation that forms the obsd. products by reaction with H2O and MeCN. Attack of H2O on the ion radical pair may also occur, but as a minor route (<3%), with formation of trans-2-methylcyclopentanol.

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