Chemistry of silyl thioketones. Part 8. Photo-induced cycloadditions of silyl thioketones with olefins

Abstract

Photo-induced cycloadditions of phenyl triphenylsilyl thioketone 1 with electron-poor olefins (acrylonitrile, methyl acrylate and cis- and trans-1,2-dichloroethene) gave silyl thietanes in a regio- and highly stereo-selective manner. In contrast, reaction with vinyl ethers gave thietanes without any regio- or stereo-control. Reaction with α-methylstyrene and 2,3-dimethylbut-2-ene gave open chain products. Desilylation of silyl thietanes occurs with prevalent inversion of configuration at the carbon bearing the silicon group.