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Catalytic autooxidation ofp-anisaldehyde and styrene by a cobaltbis-schiff base complex

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Summary

The CoII complex derived from the unsymmetricalbis-Schiff base ligand, 3-[1-[[2-[[(2-hydroxyphenyl)methylene]-amino]ethyl]amino]ethylidene]-6-methyl-2H-pyran-2,4(3H) dione H2(dha, salen), is a catalyst for the autoxidation of aromatic aldehydes. Under ambient condition Co(dha, salen) catalyses the oxidation ofp-anisaldehyde top-anisic acid in quantitative yield (250 turnovers). The presence of Co(dha, salen) also accelerates the co-oxidation ofp-anisaldehyde and styrene (88 turnovers). In the co-oxidation process, styrene is selectively converted to styrene oxide as the major product.

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References

  1. B. Bosnich, Ed.,Asymmetric Catalysis, Martimus Nijfoff, Boston, 1986, pp. 19–31.

    Google Scholar 

  2. J. T. Groves and R. S. Myers,J. Am. Chem. Soc.,105, 5791 (1983).

    Google Scholar 

  3. A. Nishinaga, H. Yomato, T. Abe, K. Maruyama and T. Matsuura,Tetrahedron Lett.,29(48), 6309 (1988).

    Google Scholar 

  4. W. Zhang, J. Locbach, S. R. Wilson and E. N. Jacobsen,J. Am. Chem. Soc.,112, 2801 (1990).

    Google Scholar 

  5. J. A. S. J. Razenberg, R. J. M. Nolte and W. Drenth, {jtJ. Chem. Soc., Chem. Commun.}, 227 (1986) and refs. therein.

  6. A. W. van der Made, M. J. P. van Gerwen, W. Drenth and R. J. M. Nolte,J. Chem. Soc. Chem. Commun., 888 (1987).

  7. D. Baluch, J. Charalambous and L. I. B. Haines,J. Chem. Soc., Chem. Commun., 1178 (1988).

  8. K. Takao, M. Wayaku, Y. Fujwara, T. Imanaka and S. Teranishi,Bull. Chem. Soc. Jpn.,43, 3898 (1970).

    Google Scholar 

  9. R. A. Budnik and J. K. Kochi,J. Org. Chem.,41(8), 1384 (1976).

    Google Scholar 

  10. S. F. Tan, K. P. Ang, L. H. Ng, A. G. Davies and D. Oprescu,Transition Met. Chem.,15, 459 (1990).

    Google Scholar 

  11. see also K. Takao, H. Azuma, Y. Fujiwara, T. Imanaka and S. Teranishi,Bull. Chem. Soc. Jpn.,45, 2003 (1972) for related work:

    Google Scholar 

  12. J. Farrar, D. Holland and D. J. Milner,J. Chem. Soc. Dalton Trans., 815 (1975).

  13. D. Holland and D. J. Milner,J. Chem. Soc. Dalton Trans., 2440 (1975).

  14. K. Kaneda, K. Jitsukawa, T. Itoh, S. Teranishi,J. Org. Chem.,45, 3004 (1980).

    Google Scholar 

  15. R. A. Sheldon, J. K. Kochi,Metal-Catalysed Oxidations of Organic Compounds, Academic Press, London-Toronto-Sydeny-San Francisco, 1981, pp. 359–363.

    Google Scholar 

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Tan, SF., Leung, Ph. & Sin, WC. Catalytic autooxidation ofp-anisaldehyde and styrene by a cobaltbis-schiff base complex. Transition Met Chem 16, 542–545 (1991). https://doi.org/10.1007/BF01024327

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  • DOI: https://doi.org/10.1007/BF01024327

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