Oxidation of Benzylic and Secondary Alcohols to Carbonyl Compounds by NaBrO₃–NH₄Cl Reagent in Aqueous Acetonitrile†

Abstract

NaBrO₃ combined with NH₄Cl is found to be an efficient reagent for the conversion, in aqueous acetonitrile and under mild conditions, of benzylic and secondary alcohols into aldehydes and ketones, respectively.

References

1. R. C. Larock, Comprehensive Organic Transformation, VCH, Weinheim, 1989.
2. M. Hudlicky, Oxidation in Organic Chemistry (ACS Monograph 186), American Chemical Society, Washington, DC, 1990.
3. A. H. Haines, Methods for Oxidation of Organic Compounds: Alcohols, Alcohol Derivatives, Alkyl Halides, Nitroalkanes, Alkyl Azides, Carbonyl Compounds, Hydroxy Arenes and Aminoarenes, Academic Press, London, 1988.
4. I. Yavari and A. Shaabani, J. Chem. Res. (S), 1994, 274.
5. (a) T.-L. Ho, Synthesis., 1978, 936; (b) H. Tomidca, K. Oshima and H. Nozaki, Tetrahedron Lett., 1982, 23, 539.
6. L. Farkas and O. Schachter, J. Am. Chem. Soc., 1949, 71, 2827.
7. K. Takase, H. Masuda, O. Kaf, Y. Nishiyama, S. Sakaguchi and Y. Ishii, Chem. Lett., 1995, 871.
8. S. Kajigaeshi, T. Nakayama, N. Nagasaki, H. Yamasaki and S. Fujisaki, Bull. Chem. Soc. Jpn., 1986, 59, 747.
9. G. Hoist, Kgl. Fysiogrof. Sallskap. Lund, 1940, 10, 63 (Chem. Abstr., 1941, 35, 78089).
10. A. C. Chatterji and S. K. Roy, Z. Phys. Chem. (Leipzig), 1972, 250, 137 (Chem. Abstr., 1972, 77, 139201z).
11. Vijayalaxmi and E. V. Sundaram, J. Indian Chem. Soc., 1978, 55, 567.
12. N. N. Greenwood and A. Earnshaw, Chemistry of the Elements., Pergamon Press, Oxford, 1984, p. 1012.
13. For an excellent review of the oxidizing power of bromine in aqueous solution, see: J. Palou, Chem. Soc. Rev., 1994, 357.
14. R. M. Roberts, J. C. Gilbert, L. B. Rodwald and A. S. Wingrove, Modern Experimental Organic Chemistry, Saunders, Philadelphia, 4th edn., 1985, pp. 700–701.
15. J. Zhang, R. L. Hertzler and E. J. Eisenbraun, J. Chem. Educ., 1992, 69, 1037.
16. W. J. Criddle and G. P. Ellis, Spectral and Chemical Characterization of Organic Compounds: A Laboratory Handbook, Wiley, Chichester, 3rd edn., 1990.
17. R. L. Wear, J. Am. Chem. Soc., 1951, 73, 2390.
18. Aldrich Catalogue/Handbook of Fine Chemicals, 1994–1995.