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An Electroinitiated Cation Chain Reaction: Intramolecular Carbon–Carbon Bond Formation between Thioacetal and Olefin Groups

Authors

  • Kouichi Matsumoto,

    1. Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigakukatsura, Nishikyo-ku, Kyoto, 615-8510, Japan, Fax: (+81) 75-383-2727
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  • Shunsuke Fujie,

    1. Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigakukatsura, Nishikyo-ku, Kyoto, 615-8510, Japan, Fax: (+81) 75-383-2727
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  • Koji Ueoka,

    1. Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigakukatsura, Nishikyo-ku, Kyoto, 615-8510, Japan, Fax: (+81) 75-383-2727
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  • Seiji Suga Dr.,

    1. Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigakukatsura, Nishikyo-ku, Kyoto, 615-8510, Japan, Fax: (+81) 75-383-2727
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  • Jun-ichi Yoshida Prof.

    1. Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigakukatsura, Nishikyo-ku, Kyoto, 615-8510, Japan, Fax: (+81) 75-383-2727
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  • This work was financially supported in part by a Grant-in-Aid for Scientific Research from the Japan Society for the Promotion of Science. We are also grateful to Nippon Shokubai Co. and Nippoh Chemicals Co. for providing sodium tetrakis(pentafluorophenyl)borate as a precursor of Bu4NB(C6F5)4.

Abstract

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Olefinische Thioacetale reagieren in Gegenwart einer katalytischen Menge an ArS(ArSSAr)+ B(C6F5)4 – oder bei der Elektrolyse in Mischungen mit ArSSAr – effizient unter intramolekularer Kohlenstoff-Kohlenstoff-Kupplung (siehe Schema). Dieses Verfahren ist aussichtsreich für elektrochemisch ausgelöste Kationenkettenreaktionen in der organischen Synthese.

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