Investigation into the Nature of the Oxoruthenate Species used to Mediate the Oxidation of an Organic Substrate by Hypochlorite in a Biphasic System†

Abstract

Hydrophilic sodium perruthenate, rather than lipophilic ruthenium tetraoxide, is the mediator in the oxidation of octan-2-ol by sodium hypochlorite in a water–carbon tetrachloride (or dichloromethane) biphasic system; as a consequence, oxidation occurs at the phase boundary and is promoted by stirring or ultrasound.

References

1. E. S. Gore, in Studies in Organic Chemistry vol. 11: Chemistry of the Platinum Group Metals, ed. F. R. Hartley, Elsevier, Amsterdam, 1991, ch. 8.
2. A. H. Haines, Methods for the Oxidation of Organic Compounds, Academic Press, London, 1988, pp. 55–64.
3. F. S. Martin, J. Chem. Soc., 1952, 2683.
4. M. Fieser, in Fieser and Fieser's Reagents for Organic Synthesis, Wiley–Interscience, 1984, 11, p. 462.
5. U. A. Spitzer and D. G. Lee, J. Org. Chem., 1974, 39, 2468.
6. W. P. Griffith, Chem. Soc. Rev., 1992, 179.
7. A. J. Bailey, L. D. Cother, W. P. Griffith and D. M. Hankin, Trans. Met. Chem., 1995, 20, 590.
8. S. Giddings and A. Mills, J. Org. Chem., 1988, 53, 1103.
9. S. Wolfe, S. K. Hasan and J. R. Campbell, J. Chem. Soc., Chem. Commun., 1970, 1420.
10. N. N. Greenwood and A. Earnshaw, Chemistry of the Elements, Pergamon, Oxford, 1984, p. 1006.
11. R. E. Connick and C. R. Hurley, J. Am. Chem. Soc., 1952, 74, 5012.
12. J. L. Woodhead and J. M. Fletcher, J. Chem. Soc., 1961, 5039.
13. R. P. Larsen and L. E. Ross, Anal. Chem., 1959, 31, 176.
14. Y. Sasson, G. D. Zappi and R. Neumann, J. Org. Chem., 1986, 51, 2880.
15. T. A. Foglia, P. A. Barr and A. J. Malloy, J. Am. Oil Chem. Soc., 1977, 54, 858A.