Mechanism of the oxidation of sulfides by dioxiranes: Conformational mobility and transannular interaction in the oxidation of thianthrene 5-oxide

Journal of Organic Chemistry

Volumn 69, Issue 26, 2004, Pages 9090-9099

  González Núñez, María Elena ^a   Mello, Rossella ^a   Royo, Jorge ^a   Asensio, Gregorio ^a   Monzó, Isidro ^a   Tomás, Francisco ^a   García López, Jesús ^b   López Ortiz, Fernando ^b  

^a UNIVERSITY OF VALENCIA   (Spain)

^b UNIVERSITY OF ALMERÍA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ISOTOPES; OXIDATION; SOLUTIONS; SOLVENTS; SULFUR COMPOUNDS;

MONOOXYGENATION; SULFIDES; TRACERS; TRANSANNULAR INTERACTION;

ORGANIC COMPOUNDS;

AMPHOLYTE; ETHYLENE OXIDE DERIVATIVE; METHYL (TRIFLUOROMETHYL)DIOXIRANE; OXIDE; OXYGEN 18; SOLVENT; SULFIDE; SULFOXIDE; SULFUR DERIVATIVE; SULFURANE DERIVATIVE; THIANTHRENE 5 OXIDE; TRACER; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATION; CONFORMATIONAL MOBILITY; ISOTOPE LABELING; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; OXYGENATION; REACTION ANALYSIS; STEREOCHEMISTRY; TRANSANNULAR INTERACTION;

EID: 10844248483     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0483062     Document Type: Article

References (58)

1. (a) Adam, W.; Hass, W.; Lohray, B. B. J. Am. Chem. Soc. 1991, 113, 6202.
2. (b) Adam, W.; Dürr, H.; Haas, W.; Lohray, B. B. Angew. Chem., Int. Ed. Engl. 1986, 25, 101.
3. (c) Adam, W.; Lohray, B. B. Angew. Chem., Int. Ed. Engl. 1986, 25, 188.
4. (d) Adam, W.; Haas, W.; Sieker, G. J. Am. Chem. Soc. 1984, 106, 5020.
5. (a) Bonchio, M.; Conte, V.; De Conciliis, M. A.; DiFuria, F.; Ballistreri, F. P.; Tommaselli, G. A.; Toscano, R. M. J. Org. Chem. 1995, 60, 4475.
6. (b) Ballistreri, F. P.; Tommaselli, G. A.; Toscano, R. M.; Bonchio, M.; Conte, V.; DiFuria, F. Tetrahedron Lett. 1994, 35, 8041.
7. (c) Ballistreri, F. P.; Tommaselli, G. A.; Toscano, R. M.; Conte, V.; DiFuria, F. J. Am. Chem. Soc. 1991, 113, 6209.
8. (d) Adam, W.; Lohray, B. B. Angew. Chem., Int. Ed. Engl. 1986, 25, 188.
9. Akasaka, T.; Haranaka, M.; Ando, W. J. Am. Chem. Soc. 1991, 113, 9898.
10. Alvarez, J. C.; Ortiz de Montellano, P. R. Biochemistry 1992, 31, 8315.
11. Hamamoto, M.; Nakayama, K.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1993, 58, 6421.
12. Plesnicar, B.; Cerkovnik, J.; Koller, J.; Kovac, F. J. Am. Chem. Soc. 1991, 113, 4946.
13. (a) Bloodworth, A. J.; Melvin, T.; Mitchell, J. C. In The Role of Oxygen in Chemistry and Biochemistry; Ando, W., Moro-oka, Y., Eds.; Studies in Organic Chemistry, Vol. 33; Elsevier. Amsterdam, 1988.
14. (b) Bloodworth, A. J.; Melvin, T.; Mitchell, J. C. J. Org. Chem. 1988, 53, 1078.
15. (a) Erzen, E.; Koller, J.; Plesnicar, B. J. Org. Chem. 2001, 66, 5155.
16. (b) Adam, W.; Golsch, D. J. Org. Chem. 1997, 62, 115.
17. Adam, W.; Chan, Y.-Y.; Cremer, D.; Gauss, J.; Sheutzow, D.; Shindler, M. J. Org. Chem. 1987, 52, 2800.
18. (a) Adam, W.; Corma, A.; García, H.; Weichold, O. J. Catal. 2000, 196, 339.
19. (b) May, B. L.; Yee, H.; Lee, D. G. Can. J. Chem. 1994, 72, 2249.
20. (a) Ballistreri, F. P.; Tomaselli, G. A.; Toscano, R. M.; Bonchio, M.; Conte, V.; DiFuria, F. Tetrahedron Lett. 1994, 35, 8041.
21. (b) Clennan, E. L.; Yang, K. J. Org. Chem. 1993, 58, 4504.
22. (c) McDouall, J. J. W. J. Org. Chem. 1992, 57, 2861.
23. (d) Ballistreri, F. P.; Tomaselli, G. A.; Toscano, R. M.; Conte, V.; DiFuria, F. J. Am. Chem. Soc. 1991, 113, 6209.
24. (a) Adam, W.; Golsch, D.; Görth, F. C. Chem. Eur. J. 1996, 2, 255.
25. (b) Adam, W.; Golsch, D. Chem. Ber. 1994, 127, 1111.
26. (a) González-Núñez, M. E.; Mello, R.; Royo, J.; Ríos, J. V.; Asensio, G. J. Am. Chem. Soc. 2002, 124, 9154.
27. (b) Asensio, G.; Mello, R.; González-Núñez, M. E. Tetrahedron Lett. 1996, 37, 2299.
28. (a) Drabowicz, J. In Chemistry of Hypervalent Compounds; Akiba, K., Ed.; Wiley-VCH: New York, 1999.
29. (b) Oae, S. Organic Sulfur Chemistry: Structure and Mechanism; CRC Press: Boca Raton, FL, 1991.
30. (c) Reed, A. E.; Schleyer, P. R. J. Am. Chem. Soc. 1990, 112, 1434.
31. (d) Hayes, R. A.; Martin, J. C. In Organic Sulfur Chemistry. Theoretical and Experimental Advances; Bernardi, F., Csizmadia, I. G., Mangini, A., Eds.; Elsevier: Amsterdam, 1985.
32. (e) Martin, J. C. Science 1983, 221, 509.
33. (f) Martin, J. C.; Paul, I. C. Science 1976, 191, 154.
34. González-Núñez, M. E.; Mello, R.; Royo, J.; Asensio, G.; Monzó, I.; Tomás, F.; García-López, J.; López-Ortiz, F., submitted to Journal of Organic Chemistry.
35. Deubel, D. V. J. Org. Chem. 2001, 66, 2686.
36. (a) Adam, W.; Bialas, J.; Hadjiarapoglou, L. Chem. Ber. 1991, 124, 2377.
37. (b) Adam, W.; Curci, R.; González-Núñez, M. E.; Mello, R. J. Am. Chem. Soc. 1991, 113, 7654.
38. Johnson, P.; Taylor, R. J. K. Tetrahedron Lett. 1997, 38, 5873.
39. (a) Mislow, K.; Schneider, P.; Ternay, A. L., Jr. J. Am. Chem. Soc. 1964, 86, 2957.
40. (b) Aroney, M. J.; Le Fèvre, R. J. W.; Saxby, J. D., J. Chem. Soc. 1965, 571.
41. (c) Mislow, K.; Chickos, K. J. Am. Chem. Soc. 1967, 89, 4815.
42. (d) Purcell, K. F.; Berschied, J. R., Jr. J. Am. Chem. Soc. 1967, 89, 1579.
43. (e) Castrillón, J. P. A.; Szmant, H. H. J. Org. Chem. 1967, 32, 976.
44. (e) Ternay, A. L., Jr.; Baack, J. C.; Chu, S. S. C.; Napoleone, V.; Martin, G.; Alfaro, C. J. Heterocycl. Chem. 1982, 19, 833.
45. (a) Zhang, J.: Saito, S.; Koizumi, T. J. Org. Chem. 1998, 63, 9375.
46. (b) Zhang, J.; Saito, S.: Koizumi, T. J. Am. Chem. Soc. 1998, 120, 1631.
47. (c) Martin, J. C.; Balthazor, T. M. J. Am. Chem. Soc. 1977, 99, 152.
48. (d) Balthazor, T. M.; Martin, J. C. J. Am. Chem. Soc. 1975, 97, 5634.
49. (e) Tullock, C. W.; Coffman, D. D.; Muetterties, E. L. J. Am. Chem. Soc. 1964, 86, 357.
50. Seeman, J. I., Chem. Rev. 1983, 83, 83
51. (a) Adzima, L. J.; Duesler, E. N.; Martin, J. C. J. Org. Chem. 1977, 42, 4001.
52. (b) Martin, L. D.; Martin, J. C. J. Am. Chem. Soc. 1977, 99, 3511.
53. (c) Martin, J. C.; Franz, J. A. J. Am. Chem. Soc. 1975, 97, 583.
54. (d) Martin, J. C.; Franz, J. A.; Arhart, R. J. J. Am. Chem. Soc. 1974, 96, 4604.
55. (e) Franz, J. A.; Martin, J. C. J. Am. Chem. Soc. 1973, 35, 2017.
56. (f) Martin, J. C.; Arhart, R. J. J. Am. Chem. Soc. 1972, 94, 5003.
57. (g) Perozzi, E.; Martin, J. C. J. Org. Chem. 1977, 42, 3222.
58. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd Ed.; Pergamon: New York, 1998.