Perfluoroalkylation of Olefins by Electrooxidation of Perfluoroalkanoic Acids: Relations between Product-Selectivity and Current Density and Structures of Olefins

DOI DOI PDF 被引用文献7件 参考文献26件
  • Uneyama Kenji
    Department of Applied Chemistry, Faculty of Engineering, Okayama University
  • Watanabe Shunsuke
    Department of Applied Chemistry, Faculty of Engineering, Okayama University
  • Tokunaga Yukio
    Department of Applied Chemistry, Faculty of Engineering, Okayama University
  • Kitagawa Kouichi
    Department of Applied Chemistry, Faculty of Engineering, Okayama University
  • Sato Yasuhiro
    Department of Applied Chemistry, Faculty of Engineering, Okayama University

書誌事項

公開日
1992
DOI
  • 10.1246/bcsj.65.1976
  • 10.1002/chin.199244036
公開者
公益社団法人 日本化学会

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説明

Electrooxidation of perfluoroalkanoic acids RfCO2H (Rf = CF3, C3F7, C7F15 together with CHF2, CH2F) in the presence of electron-deficient olefins (methyl acrylate, methyl methacrylate, acrylamide, and acrylonitrile) provided perfluoroalkylated products. The electrolysis was conducted in MeCN–H2O (7 : 1) using platinum electrodes in an undivided cell. Dimerization of methyl acrylate accompanying perfluoroalkylation, occurs in 40–50% yield under 20 mA cm−2 current density. 1,2-Addition of trifluoromethyl or difluoromethyl radicals to carbon-carbon double bond predominates in acrylamide under the high current density (100–200 mA cm−2). On the other hand, 1,2-addition of trifluoromethyl and acetamido groups and 1,2-addition of trifluoromethyl and hydroxyl groups occur in the low current density ( < 5 mA cm−2) electrolysis of methyl methacrylate.

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