Difference of Chemical Behavior of Carbon Dioxide and Carbon Disulfide on the Reaction with DBU Forming Dialkyl Carbonates and Trithiocarbonatest

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  • HORI Yuji
    Department of Industrial Chemistry, Faculty of Science and Engineering, Saga University
  • NAGANO Yoshiaki
    Department of Industrial Chemistry, Faculty of Science and Engineering, Saga University
  • FUKUHARA Takashi
    Department of Industrial Chemistry, Faculty of Science and Engineering, Saga University
  • TERAMOTO Syuji
    Department of Industrial Chemistry, Faculty of Science and Engineering, Saga University
  • TANIGUCHI Hiroshi
    Depertment of Applied Chemistry, Faculty of Engineering, Kyusyu University

Bibliographic Information

Other Title
  • DBUを用した二酸化炭素と二硫化炭素からの炭酸ジアルキルおよびチオ炭酸ジアルキル生成における反応の相違
  • Novel organic synthesis using DBU. XI. Difference of chemical behavior of carbon dioxide and carbon disulfide on the reaction with DBU forming dialkyl carbonates and trithiocarbonates.

Description

DBU absorbs CO2 effectively at room temperature in the presence of water or alcohol. Subsequently, DBU carbonate salts produced react with alkylating reagents to form the corresponding dialkyl carbonates in fairly good yields under mild reaction conditions.<BR>On the other hand, the mixture of water, CS2, and DBU (molar ra tios 2: 3: 4) gives 2moles of DBU trithiocarbonate salt, with evolution of 1 mole of CO2, by heating at 80°C and the reaction of the resulting salt with alkylating reagents affords dialkyl trithiocarbonates in good yields.<BR>The main difference between the above two cases could be ascribed to the stronger nucleophilicity of the preformed anion of sulfur than that of oxygen.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1987 (7), 1408-1413, 1987-07-10

    The Chemical Society of Japan

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