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.
1995
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].
Bonini B.F.; Franchini M.C.; Fochi M.; Mazzanti G.; Ricci A.; Zani P.; Zwanenburg B.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/899280
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