Selective Synthesis of the Iminophosphoranes and Phosphorus Ylides from (Alkylamino)phosphonium Salts. Comparative Study of Electrochemical Reduction with the Base Method

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  • OKAZAKI Yuichi
    Department of Applied Chemistry, College of Engineering, Chubu University
  • TAKEUCHI Akimasa
    Department of Applied Chemistry, College of Engineering, Chubu University
  • NINOMIYA Yoshihiko
    Department of Applied Chemistry, College of Engineering, Chubu University
  • KOKETSU Jugo
    Department of Applied Chemistry, College of Engineering, Chubu University

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Abstract

<p>Electrochemical reduction of substituted (alkylamino) phosphonium salts was carried out to confirm the generations of iminophosphoranes and phosphorus ylide, and compared with the results of the base method. The Wittig and AzaWittig reaction under the presence of benzaldehyde confirmed the generations of iminophosphoranes and phosphorus ylides. We found that it is possible to synthesize selectively both the iminophosphoranes and the phosphorus ylides from a single (alkylamino) phosphonium salt by the electrochemical reduction or by the base method under mild conditions. As a method of dehydrogenation reaction, the electrochemical reduction can play a similar role as strong bases such as sodium amide, sodium methoxide, sodium phenoxide, and DBU.</p>

Journal

  • Electrochemistry

    Electrochemistry 73 (9), 798-806, 2005-09-05

    The Electrochemical Society of Japan

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