Environmentally benign oxidation of some organic sulfides with 34% hydrogen peroxide catalyzed by simple heteropolyoxometalates

Chinese Journal of Chemistry

Volumn 25, Issue 9, 2007, Pages 1340-1343

  Tayebee, Reza ^a   Alizadeh, Mohammad Hassan ^b  

^a Sabzevar University   (Iran)

^b FERDOWSI UNIVERSITY OF MASHHAD   (Iran)

Author keywords

Catalysis; Heteropolyacid; Hydrogen peroxide; Organic sulfide; Oxidation

Indexed keywords

EID: 34548660390     PISSN: 1001604X     EISSN: None     Source Type: Journal    
DOI: 10.1002/cjoc.200790249     Document Type: Article

References (43)

1. (a) Soladie, G. Synthesis 1981, 185.
2. (b) Carreno, M. C. Chem. Rev. 1995, 95, 1917.
3. (a) Barton, D. H. R.; Li, W.; Smith, J. A. Tetrahedron Lett. 1998, 39, 7055.
4. (b) Hirano, M.; Yakabe, S.; Clark, J. H.; Morimoto, T. J. Chem. Soc., Perkin Trans. 1 1996, 2693.
5. (a) Clark, J. H. Pure Appl. Chem. 2001, 73, 103.
6. (b) Clark, J. H. Green Chem. 1999, 1, 1.
7. (c) Ghosh, A.; Gupta, S. S.; Bartos, M. J.; Hangun, Y.; Vuocolo, L. D.; Steinhoff, B. A.; Noser, C. A.; Horner, D.; Mayer, S.; Inderhees, K.; Horwitz, C. P.; Spatz, J.; Ryabov, A. D.; Mondal, S.; Collins, T. J. Pure Appl. Chem. 2001, 73, 113.
8. Lane, B. S.; Burgess, K. Chem. Rev. 2003, 103, 2457.
9. Anastas, P. T.; Warner, J. C. Green Chemistry, Theory and Practice, Oxford University Press, New York, 1998.
10. Kozhevnikov, V. In Catalysts for Fine Chemical Synthesis, Ed.: Derouane, E., Wiley, New York, 2002.
11. Nakato, S.; Kimura, M.; Okuhara, T. Chem. Lett. 1997, 389.
12. (a) Kozhevnikov, I. V. Chem. Rev. 1998, 98, 171.
13. (b) Alizadeh, M. H.; Razavi, H.; Bamoharram, F. F. J. Mol. Catal. A: Chem. 2003, 200, 105.
14. (a) Alizadeh, M. H.; Razavi, H.; Bamoharram, F. F.; Hassanzadeh, M. K.; Khoshnavazi, R.; Zonoz, F. M. Kinet. Catal. 2003, 44, 524.
15. (b) Mizuno, N.; Misono, M. J. Mol. Catal. 1994, 86, 319.
16. (a) Alizadeh, M. H.; Tayebee, R. J. Braz. Chem. Soc. 2005, 16, 108.
17. (b) Alizadeh, M. H.; Kermanil, T.; Tayebee, R. Monatsh. Chem. 2007, 138, 165.
18. (c) Alizadeh, M. H.; Tayebee, R. Monatsh. Chem. 2006, 137, 1063.
19. (d) Tayebee, R.; Rafiee, E. Bull. Chem. Soc. Ethiop. 2006, 20(2), 1.
20. Okun, N. M.; Anderson, T. M.; Hill, C. L. J. Am. Chem. Soc. 2003, 125, 3194.
21. ten Brink, G. J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 258, 1636.
22. ten Brink, G. J.; Arends, I. W. C. E.; Sheldon, R. A. Adv. Synth. Catal. 2002, 344, 355.
23. North, E. O. Inorg. Synth. 1993, 1, 129.
24. Wu, H. J. Biol. Chem. 1920, 43, 189.
25. Brevard, C.; Schimpf, R.; Tourne, G.; Tourne, C. M. J. Am. Chem. Soc. 1983, 105, 7059.
26. Fuhrhop, J.; Penzlin, G. In Organic Synthesis, Concepts, Methods, Starting Materials, 2nd Ed., VCH, Weinheim, 1994.
27. Patai, S.; Rappoport, Z. In The Chemistry of Sulphones, Sulphoxides and Sulphides, John Wiley and Sons, Chichester, U. K., 1994.
28. Uemura, S. In Comprehensive Organic Synthesis, Ed.: Ley, S. V., Pergamon, Oxford, 1991, Vol. 7, p 757.
29. Drabowski, J.; Kielbasinski, P.; Mikolajczyk, M. Synthesis of Sulfoxides, Wiley, New York, 1994.
30. Hudlicky, M. In Oxidation in Organic Chemistry, ACS Monograph 186, American Chemical Society, Washington, D. C., 1990.
31. Kakarla, R.; Dulina, R. G.; Hatzenbuhler, N. T.; Hui, Y. W.; Sofia, M. J. J. Org. Chem. 1996, 61, 8347.
32. Suarez, A. R.; Baruzzi, A. M.; Rossi, L. I. J. Org. Chem. 1998, 63, 5689.
33. Boring, E.; Geletii, Y. V.; Hill, C. L. J. Am. Chem. Soc. 2001, 123, 1625.
34. (a) Ishii, Y.; Yamawaki, T.; Ura, H.; Yamada, H.; Ogawa, M. J. Org. Chem. 1988, 53, 3587.
35. (b) Venturello, C.; D'Aloiso, R.; Bart, J. C.; Ricci, M. J. Mol. Catal. 1985, 32, 107.
36. (c) Brevard, C.; Schimpf, R.; Tourne, G.; Tourne, C. M. J. Am. Chem. Soc. 1983, 105, 7059.
37. Dimethyl sulfide is emitted steadily by ocean phytoplankton and is the major source of sulfur in the troposphere. Dimethyl sulfoxide is the first product of the aqueous phase oxidation of dimethyl sulfide by hydroperoxides and occurs in both rain and snow. Knowledge of the kinetics and mechanism of dimethyl sulfide oxidation should be helpful in understanding the contribution of dimethyl sulfide to acid rain formation and its effects on the climate. For more information see Ref. 27.
38. (a) Restelli, G.; Angeletti, G. In Dimethyl Sulfide: Oceans, Atmosphere and Climate, Ed.: Kluwer Academic, Boston, 1993.
39. (b) Andreae, M. O.; Barnard, W. R. Environ. Sci. Technol. 1983, 26, 527.
40. (c) Kiene, R. P.; Gerard, G. Mar. Chem. 1994, 47, 1.
41. (d) Ridgeway, R. G. J.; Thornton, D. C.; Bandy, A. R. J. Atmo. Chem. 1992, 14, 53.
42. (e) Andreae, M. O. Limnol. Oceanogr. 1980, 25, 1054.
43. (f) Amels, R.; Elias, H.; Wannowius, K.-J. J. Chem. Soc., Faraday Trans. 1997, 93, 2537.