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Catalysis of Cobalt Schiff Base Complexes for the Oxygenation of Olefins. Mechanisms for the Ketonization Reaction

  • A. Nishinaga
  • T. Yamada
  • H. Fujisawa
  • K. Ishizaki
  • H. Ihara
  • T. Matsuura

Abstract

Cobalt Schiff base complexes are interesting because in aprotic solvents they exhibit dioxygenase-like activities as well as the reversible formation of dioxygen complexes. Our recent findings on oxidation-reduction reactions of cobalt Schiff base complexes, Co(L1)-Co(L6), are now found to catalyze effeciently, in primary or secondary alcohols under an atmospheric pressure of O2 at 60°C, the oxygenations of olefin substrates 1, 5, and 6, which result in ketonization without carbon-carbon bond cleavage (Table 1). In the Co(L1)-catalyzed oxygenation of 1a in PhCH2OH, a mixture composed of 2a, 3a, and PhCHO was obtained. Time course of the reaction proceeded as a co-oxidation of 1a and PhCH2OH with with a 1:1 stoichiometry (98% selectivity).

Keywords

Base Complex Secondary Alcohol Aprotic Solvent Schiff Base Complex Protic Solvent 
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.
    A. Nishinaga and H. Tomita, J. Mol. Catal., 7:179 (1980).CrossRefGoogle Scholar
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    A. Nishinaga, T. Kondo and T. Natsuura, Chem. Lett., 905:1319 (1985).CrossRefGoogle Scholar
  3. 3.
    D. E. Hamilton, R. S. Drago and A. Zombeck, J. Am. Chem. Soc., 109:374 (1987).CrossRefGoogle Scholar

Copyright information

© Plenum Press, New York 1988

Authors and Affiliations

  • A. Nishinaga
    • 1
  • T. Yamada
    • 1
  • H. Fujisawa
    • 1
  • K. Ishizaki
    • 1
  • H. Ihara
    • 1
  • T. Matsuura
    • 1
  1. 1.Department of Synthetic ChemistryKyoto UniversityKyoto 606Japan

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