Tempo-catalyzed oxidations of alcohols using m-CPBA: The role of halide ions

Journal of Organic Chemistry

Volumn 64, Issue 1, 1999, Pages 310-312

  Rychnovsky, Scott D ^a   Vaidyanathan, Rajappa ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; BROMIDE; CHLORIDE ION; NITROXIDE DERIVATIVE; OXIDIZING AGENT; RADICAL;

ALCOHOL OXIDATION; ARTICLE; CATALYSIS; CATALYST; OXIDATION REDUCTION REACTION;

EID: 0033534673     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9819032     Document Type: Article

References (22)

1. (a) de Nooy, A. E. J.; Besemer, A. C.; Bekkum, H. v. Synthesis 1998, 1153-74.
2. (b) Bobbin, J. M.; Flores, M. C. L. Heterocycles 1988, 27, 509-33.
3. (a) Cella, J. A.; Kelley, J. A.; Kenehan, E. F. J. Org. Chem. 1975, 40, 1860-2.
4. (b) Cella, J. A.; McGrath, J. P.; Kelley, J. A.; El Soukkary, O.; Hilpert, L. J. Org. Chem. 1977, 42, 2077-80.
5. (c) Cella, J. A.; Kelley, J. A.; Kenehan, E. F. J. Chem. Soc., Chem. Commun. 1974, 943.
6. Ganem, B. J. Org. Chem. 1975, 40, 1998-2000.
7. (a) Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559-62.
8. (b) Anelli, P. L.; Banfi, S.; Montanari, F.; Quici, S. J. Org. Chem. 1989, 54, 2970-2.
9. (c) Anelli, P. L.; Montanari, F.; Quici, S. Org. React. 1990, 69, 212-9.
10. Einhorn, J.; Einhorn, C.; Ratajczak, F.; Pierre, J.-L. J. Org. Chem. 1996, 61, 7452-4.
11. Inokuchi, T.; Matsumoto, S.; Nishiyama, T.; Torii, S. J. Org. Chem. 1990, 55, 462-6.
12. Mico, A. D.; Margarita, R.; Parlanti, L.; Vescovi, A.; Piancatelli, G. J. Org. Chem. 1997, 62, 6974-7.
13. (a) Semmelhack, M. F.; Schmid, C. R.; Cortes, D. A.; Chou, C. S. J. Am. Chem. Soc. 1984, 106, 3374-6.
14. (b) Miyazawa, T.; Endo, T. J. Mol. Catal. 1985, 32, 357-60.
15. (a) Semmelhack, M. F.; Chou, C. S.; Cortes, D. A.; J. Am. Chem. Soc. 1983, 105, 4492-4.
16. (b) Inokuchi, T.; Matsumoto, S.; Torii, S. J. Org. Chem. 1991, 56, 2416-21.
17. (c) Kashiwagi, Y.; Yanagisawa, Y.; Kurashima, F.; Anzai, J.; Osa, T.; Bobbitt, J. M. Chem. Commun. 1996, 2745-6.
18. Rychnovsky, S. D.; Beauchamp, T.; Vaidyanathan, R.; Kwan, T. J. Org. Chem. 1998, 63, 6363-74.
19. 4NBr led to complete oxidation.
20. Lee, G. A.; Freedman, H. H. Tetrahedron Lett. 1976, 20, 1641-4.
21. The oxidation was not effective with unsaturated alcohols.
22. Hall, P. L.; Gilchrist, J. H.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 9571-4.