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Electrochemical Formation of Favorskii Rearrangement Type Intermediates and Their Reactivities

  • Toshiro Chiba
  • Isao Saitho
  • Mitsuhiro Okimoto
Conference paper

Abstract

The indirect electrooxidation of enamines of alicyclic ketones (1) in NaOMe-MeOH using iodide ion as a mediator provided ring fused cyclopropane aminoethers (2). The resulting products were then subjected to acid-catalyzed hydrolysis, alcoholysis, the reductive elimination of the methoxy group with LiAlH4, and the replacement of the methoxy group by a cyano group with Me3SiCN in the presence of a Lewis acid.

Keywords

Methoxy Group Metal Hydride Cyano Group Cyclopropane Ring Reductive Elimination 
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, H. Sakagami, M. Murata, M. Okimoto, J. Org. Chem., 1995, 60, 6764.CrossRefGoogle Scholar
  2. 2).
    (a) A. S. Kende, Org. Reactions, 1960, 11, 261;Google Scholar
  3. see also (b) J. Szmuszkovicz, E. Cerda, M. F. Grostic, J. F. Zieserl, Jr., Tetrahedron Lett., 1967, 3969.Google Scholar
  4. 3).
    H. E. Zaugg, W. B. Martin, Org. Reactions, 1965, 14, 52.Google Scholar
  5. 4).
    E. L. Eliel, R. A. Daignault, J. Org. Chem., 1965, 30, 2450.CrossRefGoogle 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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