Chromium(VI) oxide catalyzed oxidation of sulfides to sulfones with periodic acid

Journal of Organic Chemistry

Volumn 68, Issue 13, 2003, Pages 5388-5391

  Xu, Liang ^a   Cheng, Jie ^b   Trudell, Mark L ^b  

^a St Charles Pharmaceuticals Inc   (United States)

^b UNIVERSITY OF NEW ORLEANS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ATMOSPHERIC TEMPERATURE; CATALYSIS; ELECTRONS; OXIDATION; SULFIDE MINERALS;

ELECTRON DEFICIENCY;

CHROMIUM COMPOUNDS;

ACETIC ACID ETHYL ESTER; ACETONITRILE; CHROMIC OXIDE; CHROMIUM DERIVATIVE; PERIODIC ACID; SULFIDE; SULFONE; UNCLASSIFIED DRUG;

ARTICLE; OXIDATION; SOLUBILITY; STOICHIOMETRY; SYNTHESIS;

EID: 0037870789     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030031n     Document Type: Article

References (53)

1. (a) Nakayama, J.; Sugihara, Y. Top. Curr. Chem. 1999, 205, 131.
2. (b) De Lucchi, O.; Fabbri, D.; Lucchini, V. Tetrahedron 1992, 48, 1485.
3. (c) Gronowitz, S.; Nikitidis, G.; Hallberg, A.; Servin, R. J. Org. Chem. 1988, 53, 3351.
4. Paquette, L. A. Synlett 2001, 1.
5. Najera, C.; Sansano, J. M. Recent Res. Dev. Org. Chem. 1998, 2, 637.
6. Chinchilla, R.; Najera, C. Recent Res. Dev. Org. Chem. 1997, 1, 437.
7. (a) Hollingworth, G. J. In Comprehensive Organic Functional Group Transformations; Katrizky, A. R., Meth-Cohn, O., Rees, C. W., Pattenden, G., Eds.; Elsevier: Oxford, 1995.
8. (b) Patai, S., Rappoport, Z., Eds. The Synthesis of Sulphones, Sulphoxides, and Cyclic Sulphides; Wiley: New York, 1994.
9. (c) Simpkins, N. S. Sulphones in Organic Synthesis; Pergamon Press: Oxford, 1993.
10. Rozen, S.; Bareket, Y. J. Org. Chem. 1997, 62, 1457.
11. For reviews, see: (a) Fatiadi, A. J. Synthesis 1974, 229.
12. (b) Chaudhuri, B. K.; Mukherjee, H. G. J. Indian Chem. Soc. 1979, 56, 1098.
13. (a) Haines, A. H. Methods for the Oxidation of Organic Compounds, Alcohols, Alcohol Derivatives, Alkyl Halides, Nitroalkanes, Alkyl Azides, Carbonyl Compounds, Hydroxyarenes and Aminoarenes; Academic Press: London, 1988.
14. (b) Rodriguez, C. M.; Ode, J. M.; Palazon, J. M.; Martin, V. S. Tetrahedron 1992, 48, 3571.
15. (c) Nunez, M. T.; Martin, V. S. J. Org. Chem. 1990, 55, 1928.
16. (d) Wrobel, J.; Dietrich, A.; Gorham, B. J.; Sestanj, K. J. Org. Chem. 1990, 55, 2694.
17. (e) Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
18. (a) Yamazaki, S. Tetrahedron Lett. 2001, 42, 3355.
19. (b) Yamazaki, S. Org. Lett. 1999, 1, 2129.
20. (c) Zhao, M.; Li, J.; Song, Z.; Desmond, R.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. Tetrahedron Lett. 1998, 39, 5323.
21. Kim, S. S.; Nehru, K. Synlett 2002, 616.
22. Barton, D. H. R.; Li, W.; Smith, J. A. Tetrahedron Lett. 1998, 39, 7055.
23. Lee, S.; Fuchs, P. L. J. Am. Chem. Soc. 2002, 124, 13978.
24. Kim, S. S.; Nehru, K.; Kim, S. S.; Kim, D. W.; Jung, H. C. Synthesis 2002, 2484.
25. Xu, L.; Trudell, M. L. Tetrahedron Lett. 2003, 44, 2553.
26. Beckerbauer, R.; Smart, B. E. J. Org. Chem. 1995, 60, 6186.
27. Nenajdenko, V. G.; Gavryushin, A. E.; Balenkova, E. S. Tetrahedron Lett. 2001, 42, 4397.
28. (a) Chen, Q.; Duan, J. J. Chem. Soc., Chem. Commun. 1993, 918.
29. (b) Nodiff, E. A.; Lipschutz, S.; Graig, P. N.; Gordon, M. J. Org. Chem. 1960, 25, 60.
30. Su, W. Tetrahedron Lett. 1994, 35, 4955.
31. Rizzi, J. P.; Schnur, R. C.; Hutson, N. J.; Kraus, K. G.; Kelbaugh, P. R. J. Med. Chem. 1989, 32, 1208.
32. (a) Sharma, N.; Gupta, R.; Kumar, M.; Gupta, R. R. J. Fluorine Chem. 1999, 98, 153.
33. (b) Boiko, V. N.; Gogoman, I. V.; Shchupak, G. M.; Yagupolskii, L. M. Zh. Org. Khim. 1987, 23, 601.
34. (c) Kondratenko, N. V.; Kolomeitsev, A. A.; Mogilevskaya, V. O.; Varlamova, N. M.; Yagupolskii, L. M. Zh. Org. Khim. 1986, 22, 1721.
35. Sharnin, G. P.; Nurgatin, V. V. Zh. Org. Khim. 1972, 8, 1493.
36. Jones, T. R.; Varney, M. D.; Webber, S. E.; Lewis, K. K.; Marzoni, G. P.; Palmer, C. L.; Kathardekar, V.; Welsh, K. M.; Webber, S.; Matthews, D. A.; Appelt, K.; Smith, W. W.; Janson, C. A.; Villafranca, J. E.; Bacquet, R. J.; Howland, E. F.; Booth, C. L. J.; Herrmann, S. M.; Ward, R. W.; White, J.; Moomaw, E. W.; Bartlett, C. A.; Morse, C. A. J. Med. Chem. 1996, 39, 904.
37. Beaumont, A. J.; Clark, J. H. J. Fluorine Chem. 1991, 52, 295.
38. Zlotin, S. G.; Kislitsin, P. G.; Podgursky, A. I.; Samet, A. V.; Semenov, V. V.; Buchanan, A. C., III; Gakh, A. A. J. Org. Chem. 2000, 65, 8439.
39. (a) Yamada, Y. M. A.; Tabata, H.; Takahashi, H.; Ikegami, S. Synlett. 2002, 2031.
40. (b) Alonso, D. A.; Najera, C.; Varea, M. Tetrahedron Lett. 2002, 43, 3459.
41. (c) Choi, S.; Yang, J. D.; Ji, M.; Choi, H.; Kee, M.; Ahn, K. H.; Byeon, S. H.; Baik, W.; Koo, S. J. Org. Chem. 2001, 66, 8192.
42. (d) Sato, K.; Hyodo, M.; Aoki, M.; Zheng, X.; Noyori, R. Tetrahedron 2001, 57, 2469.
43. (e) Van Dort, P. C.; Fuchs, P. L. J. Am. Chem. Soc. 1994, 116, 5657.
44. (a) Loughlin, W. A.; Rowen, C. C.; Healy, P. C. J. Chem. Soc., Perkin Trans. 2 2002, 296.
45. (b) Kurtner, A.; Chodynski, M.; Halkes, S. J. Synth. Commun. 1996, 26, 1175.
46. (c) Davis, F.; Zhou, P. Tetrahedron Lett. 1994, 35, 7525.
47. (a) Patonay, T.; Adam, W.; Levai, A.; Kover, P.; Nemeth, M.; Peters, E. M.; Peters, K. J. Org. Chem. 2001, 66, 2275.
48. (b) Marchan, V.; Gibert, M.; Messeguer, A.; Pedroso, E.; Grandas, A. Synthesis 1999, 43.
49. Fringuelli, F.; Pellegrino, R.; Piermatti, O.; Pizzo, F. Synth. Commun. 1994, 24, 2665.
50. (a) Webb, K. S. Tetrahedron Lett. 1994, 35, 3457.
51. (b) Trost, B. M.; Curran, D. P. Tetrahedron Lett. 1981, 22, 1287.
52. Khanapure, S. P.; Powell, W. S.; Rokach, J. J. Org. Chem. 1998, 63, 8976.
53. Arnauld, T.; Barrett, A. G. M.; Cramp, S. M.; Roberts, R. S.; Zecri, F. J. Org. Lett. 2000, 2, 2663.