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Electro-Oxidation of Enamines Using Iodide Ion as a Mediator

  • Toshiro Chiba
  • Isao Saitho
  • Mitsuhiro Okimoto

Abstract

A series of pyrrolidinoenamines of an alicyclic ketone (1) was subjected to the indirect electrooxidation in NaCN-MeOH using iodide ion as a mediator. It was found that the electrolysis products were dependent on the ring size of the ketone component. For example, the cyclohexanone and cycloheptanone enamines exclusively provided a ring fused cyclopropane aminonitrile (2),whereas the cyclooctanone enamine yielded only the corresponding β-cyanoenamine (4).

Keywords

Trans Isomer Ring Size Pyrrolidine Ring Sodium Cyanide Electrolysis Product 
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.

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References

  1. 1).
    T. Chiba, M. Okimoto, H. Nagai, Y. Takata, J. Org. Chem., 1979, 44, 3519. see also; T. Shono, Y. Matsumura, H. Hamaguchi, T. Imanishi, K. Yoshida, Bull. Chem. Soc. Jpn., 1978, 86, 2101.Google Scholar
  2. 2).
    J. Szmuszkovicz, E. Cerda, M. F. Grostic, J. F. Zieserl, Jr., Tetrahedron Lett, 1967, 3969.Google Scholar
  3. 3).
    C. Kaizer, J. Weinstock, Org. Synth., 1988, 6, 910.Google Scholar
  4. 4).
    P. A. S. Smith, Org. Reactions, 1946, 3, 337.Google Scholar

Copyright information

© Springer Japan 1998

Authors and Affiliations

  • Toshiro Chiba
    • 1
  • Isao Saitho
    • 1
  • Mitsuhiro Okimoto
    • 1
  1. 1.Department of Applied ChemistryKitami Institute of TechnologyKitamiJapan 090

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