Heterogeneously catalysed cleavage of carbon–carbon double bonds with hydrogen peroxide using calcined heteropolyacids on oxide supports

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Christopher D. Brooks, Ling-chu Huang, Moya McCarron and Robert A. W. Johnstone


Abstract

Reaction of an alkene with aqueous hydrogen peroxide and a catalytic quantity of a heteropolyacid adsorbed onto magnesium, aluminium or zinc oxide leads to complete, rapid cleavage of the alkene to give carbonyl compounds.


References

  1. For general discussions of alkene cleavage see, J. March, Advanced Organic Chemistry, Wiley, New York, 1992, pp. 1177–1182 Search PubMed; P. M. Henry and G. L. Lange, in The Chemistry of Functional Groups, Suppl. A, Part I, ed, S. Patai, Wiley, New York, 1977, pp. 965–1098 Search PubMed; M. Hudlicky, Oxidation of Organic Compounds, ACS Monograph, ACS, Washington, 1990, pp. 77–84 Search PubMed.
  2. Y. Izumi, K. Urabe and M. Onaka, Zeolite, Clay and Heteropolyacids, Kondasha, Tokyo, 1992, p. 163 Search PubMed.
  3. (a) M. Schwegler, M. Floor and H. van Bekkum, Tetrahedron Lett., 1988, 29, 823 CrossRef CAS; (b) Y. Ishii, K. Yamakawaki, T. Ura, H. Yamada and M. Ogawa, J. Org. Chem., 1988, 53, 3587 CrossRef CAS; (c) H. Furukawa, T. Nakamura, H. Inagaki, E. Nishikawa, C. Imai and M. Misono, Chem. Lett., 1988, 877 CAS.
  4. Y. Uzumi and K. Hayashi, Chem. Lett., 1980, 789.
  5. C. W. Smith and R. T. Holm, J.Org.Chem., 1957, 22, 746 CrossRef CAS.
  6. M. Misono, N. Mizuno, K. Katamura, A. Kisai, Y. Konishi, K. Sakata, T. Okuhara and Y. Yoneda, Bull. Chem. Soc. Jpn., 1982, 55, 400 CAS.
  7. J. R. Schaeffer and A. O. Snoddy, Org. Synth., 1963, Coll. Vol. 4, 9.
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