Sulfide and sulfoxide oxidations by Mono- and Diperoxo complexes of molybdenum. A density functional study

Journal of Organic Chemistry

Volumn 68, Issue 15, 2003, Pages 5870-5874

  Sensato, Fabrício R ^a   Custodio, Rogério ^a   Longo, E ^b   Safont, Vicent S ^c   Andres, Juan ^c  

^a UNIVERSITY OF CAMPINAS   (Brazil)

^b FEDERAL UNIVERSITY OF SÃO CARLOS   (Brazil)

^c UNIVERSITAT JAUME I   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; DECOMPOSITION; MOLYBDENUM; OXIDATION; PROBABILITY DENSITY FUNCTION; THERMODYNAMICS;

MOLECULAR MECHANISM;

SULFUR COMPOUNDS;

MOLYBDENUM; OXIDIZING AGENT; SULFIDE; SULFOXIDE;

ARTICLE; CALCULATION; CHEMICAL REACTION KINETICS; COMPLEX FORMATION; DECOMPOSITION; MOLECULAR MECHANICS; OXIDATION; THERMODYNAMICS;

EID: 0038711419     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034261d     Document Type: Article

References (46)

1. Prilezhaeva, E. N. Russ. Chem. Rev. 2001, 70, 897-920.
2. Page, P. C. B., Ed. Organosulfur Chemistry I; Springer: Berlin, 1999.
3. Page, P. C. B., Ed. Organosulfur Chemistry II; Springer: Berlin, 1999.
4. Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760.
5. Oae, S. Organic sulfur chemistry: Structure and mechanism; CRC: Boca Raton, FL, 1991.
6. Batigalhia, F.; Zaldini-Hernandes, M.; Ferreira, A. G.; Malvestiti, I.; Cass, Q. B. Tetrahedron 2001, 57, 9669-9676.
7. Mimoun, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 734-750.
8. Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford Univesity Press: Oxford, 1998.
9. Anastas, P. T.; Kirchhoff, M. M. Acc. Chem. Res. 2002, 35, 686-694.
10. Dickman, M. H.; Pope, M. T. Chem. Rev. 1994, 94, 569-584.
11. Jorgensen, K. A. Chem. Rev. 1989, 89, 431-364.
12. Deubel, D. V.; Sundermeyer, J.; Frenking, G. J. Am. Chem. Soc. 2000, 122, 10101-10108.
13. Deubel, D. V.; Frenking, G.; Senn, H. M.; Sundermeyer, J. Chem. Commun. 2000, 2469-2470.
14. Deubel, D. V.; Sundermeyer, J.; Frenking, G. Inorg. Chem. 2000, 39, 2314-2320.
15. Deubel, D. V.; Sundermeyer, J.; Frenking, G. Org. Lett. 2001, 3, 329-332.
16. Deubel, D. V.; Sundermeyer, J.; Frenking, G. Eur. J. Inorg. Chem. 2001, 1819-1827.
17. Deubel, D. V. J. Phys. Chem. A 2001, 105, 4765-4772.
18. Di Valentin, C.; Gisdakis, P.; Yudanov, I. V.; Rösch, N. J. Org. Chem. 2000, 65, 2996-3004.
19. Filatov, M.; Shalyaev, K.; Talsi, E. J. Mol. Catal. 1994, 87, L5-L9.
20. Gisdakis, P.; Yudanov, I. V.; Rösch, N. Inorg. Chem. 2001, 40, 3755-3765.
21. Hrock, A.; Gemmecker, G.; Thiel, W. Eur. J. Inorg. Chem. 2000, 5, 1107-1114.
22. Jorgensen, K. A.; Hoffmann, R. Acta Chem. Scand. B 1986, 40, 411-419.
23. Macchi, P.; Schultz, A. J.; Larsen, F. K.; Iversen, B. B. J. Phys. Chem. A 2001, 105, 9231-9242.
24. Salles, L.; Piquemal, J. I.; Thouvenot, R.; Minot, C.; Bregeault, J. M. J. Mol. Catal. A Chem. 1997, 117, 375-387.
25. Sensato, F. R.; Cass, Q. B.; Longo, E.; Zuckerman-Schpector, J.; Custodio, R.; Andrés, J.; Zaldini-Hernandes, M.; Longo, R. L. Inorg. Chem. 2001, 40, 6022-6025.
26. Sensato, F. R.; Custodio, R.; Cass, Q. B.; Longo, E.; Zaldini-Hernandes, M.; Longo, R. L.; Andres, J. THEOCHEM 2002, 589-590, 251-264.
27. Yudanov, I. V.; Di Valentin, C.; Gisdakis, P.; Rösch, N. J. Mol. Catal. A: Chem. 2000, 158, 189-197.
28. Sharpless, K. B.; Townsend, J. M.; Williams, D. R. J. Am. Chem. Soc. 1972, 94, 295-296.
29. Bonchio, M.; Conte, V.; De Conciliis, M. A.; Di Furia, F.; Ballistreri, F. P.; Tomaselli, G. A.; Toscano, R. M. J. Org. Chem. 1995, 60, 4475-4480.
30. Campestrini, S.; Conte, C.; Di Furia, F.; Modena, G.; Bortolini, O. J. Org. Chem. 1988, 53, 5721-5724.
31. Butler, A.; Clague, M. J.; Meister, G. E. Chem. Rev. 1994, 94, 625-638.
32. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
33. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5642.
34. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Milam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaroni, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian98, Revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
35. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299-310.
36. Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154-2161.
37. Farrugia, L. J. J. Appl. Crystallogr. 1997, 565.
38. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926.
39. Dapprich, S.; Frenking, G. J. Phys. Chem. 1995, 99, 9352-9362.
40. As a matter of fact, the direct formation of sulfones without participation of the corresponding sulfoxide could not be ruled out. A very recent mechanistic study on the oxidation of sulfides by dioxiranes claims that the reactants form a reactive intermediate that can either evolve into the respective sulfoxide or undergo further oxidation to yield the corresponding sulfone (González-Núnez, M. E.; Mello, R.; Royo, J.; Ríos, J. V.; Asensio, G. J. Am. Chem. Soc. 2002, 124, 9154-9163).
41. Keilen, G.; Benneche, T.; Gaare, K.; Undheim, K. Acta Chem. Scand. 1992, 46, 867-871.
42. The ratio d/b is a measure of the electronic character of the oxidant. If d/b > 1, the oxidant is eletrophilic. If d/b < 1, the oxidant is nucleophilic.
43. Ballistreri, F. P.; Tomaselli, G. A.; Toscano, R. M.; Conte, V.; Di Furia, F. J. Am. Chem. Soc. 1991, 113, 6209-6212.
44. Adam, W.; Wolfgang, H.; Sieker, G. J. Am. Chem. Soc. 1984, 106, 5020-5022.
45. Adam, W.; Haas, W.; Lohray, B. B. J. Am. Chem. Soc. 1991, 113, 6202-6208.
46. In a recent study on ethylene epoxidation by oxo-diperoxo complexes of transition metals, Rosch et al. found a linear correlation between the energy of the σ*(O-O) level of the complex and the height of the activation barrier: for a fixed electron donor, the higher the energy of the σ*(O-O) level, the higher the activation energy.