MTO catalyzed oxidation of aldehyde N,N-dimethylhydrazones with hydrogen peroxide: high yield formation of nitriles and N-methylene-N-methyl N-oxide

Abstract

N,N-Dimethylhydrazones of aldehydes react with hydrogen peroxide at –50 °C in the presence of catalytic amounts of methyltrioxorhenium (MTO) to give in high yield the corresponding nitriles and N-methylene-N-methyl N-oxide.

References

1. D. Barton and W. D. Ollis, in Comprehensive Organic Chemistry, Pergamon, Oxford, UK, 1979, vol. 2, ch. 8, pp. 534–535.
2. R. F. Smith, J. A. Albright and A. M. Waring, J. Org. Chem., 1966, 31, 4100.
3. A. Altamura, L. D'Accolti, A. Detomaso, A. Dinoi, M. Fiorentino, C. Fusco and R. Curci, Tetrahedron Lett., 1998, 39, 2009.
4. R. Fernandez, C. Gasch, J. M. Lassaletta, J. M. Llera and J. Vazquez, Tetrahedron Lett., 1993, 34, 141.
5. S. I. Murahashi, T. Shiota and Y. Imada, in Organic Synthesis, Wiley, New York, 1991, vol. 70, pp. 265–271.
6. W. A. Herrmann and F. Kühn, Acc. Chem. Res., 1997, 30, 169.
7. H. Rudler, J. Ribeiro Gregorio, B. Denise and J. Vaissermann, J. Organomet. Chem., 1997, 548, 295.
8. H. Rudler, J. Ribeiro Gregorio, Bernard Denise, J. M. Brégeault and A. Deloffre, J. Mol. Catal. A, Chem., 1998, in the press.
9. W. A. Herrmann, R. W. Fischer, W. Scherer and M. U. Rauch, Angew. Chem., Int. Ed. Engl., 1993, 32, 1157.
10. A. M. Al-Ajlouni and J. H. Espenson, J. Org. Chem., 1996, 61, 3969.
11. T. H. Zauche and J. H. Espenson, Inorg. Chem., 1997, 36, 5257.
12. Z. Zhu and J. H. Espenson, J. Org. Chem., 1995, 60, 1326.
13. R. W. Murray, K. Iyanar, J. Chen and J. T. Wearing, Tetrahedron Lett., 1996, 37, 805.
14. A. Goti and L. Nannelli, Tetrahedron Lett., 1996, 37, 6025.
15. M. Yamashita, K. Matsumiya and K. Nakano, Bull. Chem. Soc. Jpn., 1993, 66, 4100.