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.
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.; Zwanenburg B.. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - STAMPA. - 1995:16(1995), pp. 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.
