A mild oxidative transformation of nitro compounds into ketones by tetrapropylammonium perruthenate

Abstract

Oxidation of secondary nitro compounds with a catalytic amount of tetrapropylammonium perruthenate in the presence of N-methylmorpholine N-oxide, silver(I) acetate, potassium carbonate and 4 Å molecular sieves provides the corresponding ketones in moderate to good yields.

References

1. W. E. Noland, Chem. Rev., 1955, 55, 137.
2. (a) J. E. McMurry and J. Melton, J. Am. Chem. Soc., 1971, 93, 5309; J. Org. Chem., 1973, 38, 4367; (b) R. Kirchhoff, Tetrahedron Lett., 1976, 2533.
3. (a) A. H. Pagano and H. Shechter, J. Org. Chem., 1970, 35, 295; (b) H. Schechter and F. T. Williams, J. Org. Chem., 1962, 27, 3699; (c) J. E. McMurry, J. Melton and H. Padgett, J. Org. Chem., 1974, 39, 259; (d) N. Kornblum and P. A. Wade, J. Org. Chem., 1973, 38, 1418; (e) J. M. Aizpurua, M. Oiarbide and C. Palomo, Tetrahedron Lett., 1987, 28, 5361; (f) P. A. Bartlett, F. R. Green III and T. R. Webb, Tetrahedron Lett., 1977, 331; (g) G. A. Olah, M. Arvanaghi, Y. D. Vankar and G. K. S. Prakash, Synthesis, 1980, 44; (h) G. A. Olah and B. G. B. Gupta, Synthesis, 1980, 662; (i) M. R. Galobardes and H. W. Pinnick, Tetrahedron Lett., 1981, 22, 5235.
4. E. Keinan and Y. Mazur, J. Am. Chem. Soc., 1977, 99, 3861.
5. (a) W. P. Griffith, S. V. Ley, G. P. Whitcombe and A. D. White, J. Chem. Soc., Chem. Commun., 1987, 1625; (b) S. V. Ley, J. Norman, W. P. Griffith and S. P. Marsden, Synthesis, 1994, 639.
6. K. R. Guertin and A. S. Kende, Tetrahedron Lett., 1993, 34, 5369.
7. A. Goti and M. Romani, Tetrahedron Lett., 1994, 35, 6567.
8. A. Goti, F. D. Sarlo and M. Romani, Tetrahedron Lett., 1994, 35, 6571.
9. Clare et al. reported a failure of the oxidation of nitro alcohol with a catalytic amount of tetrapropylammonium perruthenate in the presence of N-methylmorpholine N-oxide: B. W. Clare, V. Ferro, B. W. Skelton, R. V. Strick and A. H. White, Aust. J. Chem., 1993, 46, 805.
10. Y. Tokunaga, M. Yagihashi, M. Ihara and K. Fukumoto, J. Chem. Soc., Chem. Commun., 1995, 955.
11. J. M. Aizpurua, M. Oiarbide and C. Palomo, Tetrahedron Lett., 1987, 28, 5361.
12. R. W. Fitch and F. A. Luzzio, Tetrahedron Lett., 1994, 35, 6013.