Methyltrioxorhenium-Catalyzed Oxidation of Secondary and Primary Amines with Hydrogen Peroxide

Bulletin of the Chemical Society of Japan

Volumn 70, Issue 4, 1997, Pages 877-883

  Yamazaki, Shigekazu ^a  

^a TOYAMA INDUSTRIAL TECHNOLOGY CENTER   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001591506     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.70.877     Document Type: Article

References (56)

1. a) W. A. Herrmann, R. W. Fischer, and D. W. Marz. Angew. Chem., Int. Ed. Engl., 30, 1638 (1991);
2. b) W. A. Herrmann, R. W. Fischer, M. U. Rauch, and W. Scherer, J. Mol. Catal, 86, 243 (1994);
3. c) A. M. AI-Ajlouni and J. H. Espenson, J. Am. Chem. Soc., 117, 9243 (1995);
4. d) A. M. Al-Ajlouni and J. H. Espenson, J. Org. Chem., 61, 3969 (1996).
5. Z. Zhu and J. H. Espenson, J. Org. Chem., 60, 7728 (1995).
6. a) W. Adam, W. A. Herrmann, J. Lin, C. R. Saha-Möller, R. W. Fischer, and J. D. G. Correia, Angew. Chem., Int. Ed. Engl, 33, 2475 (1994);
7. b) W. Adam, W. A. Herrmann, C. R. Saha-Möller, and M. Shimizu, J. Mol. Catal. A: Chem., 97, 15 (1995).
8. W. Adam, W. A. Herrmann, J. Lin, and C. R. Saha-Möller, J. Org. Chem., 59, 8281 (1994).
9. W. A. Herrmann, R. W. Fischer, and J. D. G. Correia, J. Mol. Catal., 94, 213 (1994).
10. S. Yamazaki, Chem. Lett., 1995, 127.
11. a) P. Huston, J. H. Espenson, and A. Bakac, Inorg. Chem., 32, 4517 (1993);
12. b) K. A. Vassell and J. H. Espenson, Inorg. Chem., 33, 5491 (1994);
13. c) W. Adam, C. M. Mitchell, and C. R. Saha-Möller, Tetrahedron, 50, 13121 (1994);
14. d) S. Yamazaki, Bull. Chem. Soc: Jpn., 69, 2955 (1996);
15. e) K. N. Brown and J. H. Espenson, Inorg. Chem.,35, 7211 (1996).
16. Z. Zhu and J. H. Espenson, J. Org. Chem., 60, 1326 (1995).
17. R. W. Murray, K. lyanar, J. Chen, and J. T. Wearing, Tetrahedron Lett.,37, 805 (1996).
18. R. W. Murray, K. lyanar, J. Chen, and J. T. Wearing, Tetrahedron Lett., 36, 6415 (1995).
19. M. M. Abu-Omar and J. H. Espenson, J. Am. Chem. Soc., 117, 272 (1995).
20. J. H. Espenson, O. Pestovsky, P. Huston, and S. Staudt, J. Am. Chem. Soc., 116, 2869 (1994).
21. P. J. Hansen and J. H. Espenson, Inorg. Chem., 34, 5839 (1995).
22. W. A. Herrmann, R. W. Fischer, W. Scherer, and M. U. Rauch, Angew. Chem., Int. Ed. Engl, 32, 1157 (1993).
23. S. Yamazaki, J. H. Espenson, and P. Huston, Inorg. Chem., 32, 4683 (1993).
24. M. M. Abu-Omar, P. J. Hansen, and J. H. Espenson, J. Am. Chem. Soc., 118, 4966 (1996).
25. a) R. A. Sheldon and J. K. Kochi, "Metal-Catalyzed Oxidations of Organic Compounds," Academic Press, New York (1981), p. 388;
26. b) M. Hudlicky, "Oxidations in Organic Chemistry," American Chemical Society, Washington, D.C. (1990), p. 234.
27. a) Parts of the results have been presented at "the28th Symposium on Oxidation Reactions," Osaka, November, 1995, Abstr., p. 77-80;
28. b) A MTO-catalyzed oxidation of secondary amines to nitrones have been very recently reported just before submission of this manuscript: A. Goti and L. Nannelli, Tetrahedron Lett., 37, 6025 (1996);
29. c) Since submission of this manuscript another report has appeared describing simillar results: R. W. Murray, K. lyanar. J. Chen, and J. T. Wearing, J. Org. Chem., 61, 8099 (1996).
30. a) S. -I. Murahashi, T. Shiota, and Y. Imada, Org. Synth., 70, 265 (1991);
31. b) S. -I. Murahashi, H. Mistui, T. Shiota, T. Tsuda, and S. Watanabe, J. Org. Chem., 55, 1736 (1990);
32. c) H. Mitsui, S. Zenki, T. Shiota, and S. -I. Murahashi, J. Chem. Soc., Chem. Commun., 1984. 874.
33. S. -I. Murahashi and T. Shiota, Tetrahedron Lett., 28, 2383 (1987).
34. a) S. Sakaue, Y. Sakata, Y. Nishiyama, and Y. Ishii, Chem. Lett., 1992, 289;
35. b) F. P. Ballistreri, U. Chiacchio, A. Rescifina, G. A. Tomaselli, and R. M. Toscano, Tetrahedron, 48, 8677 (1992).
36. E. Marcantoni, M. Petrini, and O. Polimanti, Tetrahedron Lett.,36, 3561 (1995).
37. R. Joseph, A. Sudalai, and T. Ravindranathan, Synlett. 1995, 1177.
38. R. W. Murray and M. Singh, J. Org. Chem., 55, 2954 (1990).
39. a) W. W. Zajac, Jr., T. R. Walters, and M. G. Darcy, J. Org. Chem., 53, 5856 (1988);
40. b) G. Hanquet and X. Lusinchi, Tetrahedron, 50, 12185 (1994).
41. A. Brandi, S. Garro, A. Guarna, A. Goti, F. Cordero, and F. DeSarlo, J. Org. Chem., 53, 2430 (1988).
42. J. K. Crandall and T. Reix, J. Org. Chem., 57, 6759 (1992).
43. a) R. W. Murray, R. Jeyaraman, and L. Mohan, Tetrahedron Lett., 27, 2335 (1986);
44. b) R. W. Murray, S. N. Rajadhyaksha, and L. Mohan, J. Org. Chem., 54, 5783 (1989);
45. c) D. L. Zabrowski. A. K. Moormann, and K. R. Beck, Jr., Tetrahedron Lett., 28, 4501 (1988).
46. S. Surcsh, R. Joseph, B. Jayachandran, A. V. Pol, M. P. Vinod, A. Sudalai, H. R. Sonawane, and T. Ravindranathan, Tetrahedron. 51, 11305 (1995).
47. S. Sakaue, T. Tsubakino, Y. Nishiyama, and Y. Ishii, J. Org. Chem., 58, 3633 (1993).
48. a) P. Burckard, J. Fleury, and F. Weiss, Bull. Chim. Soc. Fr., 10, 2730 (1965);
49. b) K. Kahr and C. Berther, Chem. Her., 93, 132 (1960).
50. W. A. Herrmann, F. E. Kühn, R. W. Fischer, W. R. Thiel, and C. C. Romao, Inorg. Chem., 31, 4431 (1992).
51. J. R. Falck, L. L. Miller, and F. R. Stermitz, Tetrahedron, 30, 931 (1974).
52. G. Bartoli, E. Marcantoni, and M. Petrini, J. Org. Chem., 57, 5834 (1992).
53. S. Franco, F. L. Merchán, P. Merino, and T. Tejero, Synth. Commun.,25, 2275 (1995).
54. R. W. Murray and M. Singh. Symh. Commun., 19, 3509 (1989).
55. W. W. Zajac. Jr., T. R. Walters, and J. M. Wood, Synthesis, 1988, 808.
56. "Dictionary of Organic Compounds," 5th ed, ed by J. Buckingham, Chapman & Hall, New York (1992).