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New and Convenient Synthesis of 3-Methylene-4-Pentenoic Acid by Electrochemical Carboxylation

  • Hisanori Senboku
  • Yusuke Fujimura
  • Akihiro Yoshikawa
  • Hiroshi Suginome
  • Masao Tokuda

Abstract

Electrochemical carboxylation of 2-bromomethyl-1,4-dibromo-2-butene (1) with atmospheric carbon dioxide in a DMF solution containing Bu4NI with a Pt cathode and a manganin alloy or nickel anode gave 3-methylene-4-pentenoic acid (2) in 57% yield. The acid 2 can be used as a diene in an aqueous intermolecular Diels-Alder reaction with dimethyl fumarate to give the adduct 4 in 67% yield.

Keywords

Atmospheric Carbon Dioxide Anode Current Density Zinc Powder Dimethyl Fumarate Density Electrolyte 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Reference

  1. 1).
    M. Tokuda, N. Mimura, T. Karasawa, H. Fujita, and H. Suginome, Tetrahedron Lett, 1993, 34, 7607.CrossRefGoogle Scholar
  2. 2).
    M. Tokuda, N. Mimura, K. Yoshioka, T. Karasawa, H. Fujita, and H. Suginome, Synthesis, 1993, 1086.Google Scholar
  3. 3).
    P. A. Grieco, Aldrichimica Acta, 1991, 24, 59, and the references cited therein.Google Scholar

Copyright information

© Springer Japan 1998

Authors and Affiliations

  • Hisanori Senboku
    • 1
  • Yusuke Fujimura
    • 1
  • Akihiro Yoshikawa
    • 1
  • Hiroshi Suginome
    • 1
  • Masao Tokuda
    • 1
  1. 1.Division of Molecular Chemistry, Graduate School of EngineeringHokkaido UniversitySapporo 060Japan

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