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.
Bonini B.F., Franchini M.C., Fochi M., Mazzanti G., Ricci A., Zani P., et al. (1995). Chemistry of silyl thioketones. Part 8. Photo-induced cycloadditions of silyl thioketones with olefins. JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I, 1995(16), 2039-2044 [10.1039/p19950002039].
Chemistry of silyl thioketones. Part 8. Photo-induced cycloadditions of silyl thioketones with olefins
Bonini B. F.;Franchini M. C.;Fochi M.;Mazzanti G.;Ricci A.;Zani P.;
1995
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
