Synthesis of nitrones by methyltrioxorhenium catalyzed direct oxidation of secondary amines

Tetrahedron Letters

Volumn 37, Issue 33, 1996, Pages 6025-6028

  Goti, Andrea ^a   Nannelli, Luca ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; HYDROGEN PEROXIDE; METHYLTRIOXORHENIUM; NITRONE DERIVATIVE; RHENIUM COMPLEX; UNCLASSIFIED DRUG; UREA;

ARTICLE; CATALYSIS; ENVIRONMENTAL TEMPERATURE; OXIDATION;

EID: 0030581336     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01266-X     Document Type: Article

References (32)

1. 1. Goti, A.; Romani, M. Tetrahedron Lett. 1994, 35, 6567-6570.
2. 2. Goti, A.; De Sarlo, F.; Romani, M. Tetrahedron Lett. 1994, 35, 6571-6574.
3. 3. (a) Tufariello, J. J. In "1,3-Dipolar Cycloaddition Chemistry", Padwa, A.; Ed.; John Wiley & Sons: New York, 1984.
4. (b) Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1-173.
5. (c) Torssell, K. B. G. "Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis"; Feuer, H., Ed.; VCH Publishers: New York, 1988.
6. (d) Döpp, D.; Döpp, H. In "Houben-Weyl - Methoden der organischen Chemie", vol. E14b, Klamann, D.; Hagemann, H.; Eds.; Georg Thieme Verlag: Stuttgart, 1990.
7. (e) Breuer, E. In "The Chemistry of Amino, Nitroso and Nitro Compounds and Their Derivatives", Patai, S.; Ed.; Wiley Interscience: New York, 1982.
8. 4. (a) Murahashi, S.-I.; Mitsui, H.; Shiota, T.; Tsuda, T.; Watanabe, S. J. Org. Chem. 1990, 55, 1736-1744.
9. (b) Ballistreri, F. P.; Chiacchio, U.; Rescifina, A.; Tomaselli, G. A.; Toscano, R. M. Tetrahedron 1992, 48, 8677-8684.
10. (c) Sakaue, S.; Sakata, Y.; Nishiyama, Y.; Ishii, Y. Chem. Lett. 1992, 289-292.
11. (d) Murahashi, S.-I.; Shiota, T. Tetrahedron Lett. 1987, 28, 2383-2386.
12. 5. (a) Zajac, Jr., W. W.; Walters, T. R.; Darcy, M. G. J. Org. Chem. 1988, 53, 5856-5860.
13. (b) Murray, R. W.; Singh, M. J. Org. Chem. 1990, 55, 2954-2957.
14. 6. Marcantoni, E.; Petrini, M.; Polimanti, O. Tetrahedron Lett. 1995, 36, 3561-3562.
15. 7. Goti, A.; Cicchi, S.; Cardona, F.; Brandi, A. unpublished results.
16. 8. Murahashi, S.-I. Pure Appl. Chem. 1992, 64, 403-412.
17. 9. (a) Herrmann, W. A.; Fischer, R. W.; Scherer, W.; Rauch, M. U. Angew. Chem., Int. Ed. Engl. 1993, 32, 1157-1160.
18. (b) Yamazaki, S.; Espenson, J. H.; Huston, P. Inorg. Chem. 1993, 32, 4683-4687.
19. 10. (a) Herrmann, W. A.; Fischer, R. W.; Marz, D. W. Angew. Chem., Int. Ed. Engl. 1991, 30, 1638-1641.
20. (b) Herrmann, W. A.; Fischer, R. W.; Rauch, M. U.; Scherer, W. J. Mol. Catal. 1994, 86, 243-266.
21. 11. Adam, W.; Herrmann, W. A.; Lin, J.; Saha-Möller, C. R.; Fischer, R. W.; Correia, J. D. G. Angew. Chem., Int. Ed. Engl. 1994, 33, 2475-2477.
22. 12. Adam, W.; Herrmann, W. A.; Lin, J.; Saha-Möller, C. R. J. Org. Chem. 1994, 59, 8281-8283.
23. 13. Yamazaki, S. Chem. Lett. 1995, 127-128.
24. 14 (a) Adam, W.; Mitchell, C. M.; Saha-Möller, C. R Tetrahedron 1994, 50, 13121-13124.
25. (b) Vassell, K. A.; Espenson, J. H. Inorg. Chem. 1994, 33, 5491-5498.
26. 15. Zhu, Z.; Espenson, J. H. J. Org. Chem. 1995, 60, 1326-1332.
27. 16. Abu-Omar, M. M.; Espenson, J. H. J. Am. Chem. Soc. 1995, 117, 272-280.
28. 17. Murray, R. W.; Iyanar, K.; Chen, J.; Wearing, J. T. Tetrahedron Lett. 1995, 36, 6415-6418.
29. 18. Boehlow, T. R.; Spilling, C. D. Tetrahedron Lett. 1996, 37, 2717-2720.
30. 19. Adam, W.; Mitchell, C. M. Angew. Chem., Int. Ed. Engl. 1996, 55, 533-535.
31. 20. Murray, R. W.; Iyanar, K.; Chen, J.; Wearing, J. T. Tetrahedron Lett. 1996, 37, 805-808.
32. 2 and the undissolved urea filtered off. The pure nitrones were collected by chromatography on silica gel using the appropriate eluent.