Dinitrogen tetroxide impregnated charcoal (N2O 4/Charcoal): Selective oxidation of thiols to disulfides or thiosulfonates

Phosphorus, Sulfur and Silicon and the Related Elements

Volumn 181, Issue 3, 2006, Pages 473-479

  Iranpoor, Nasser ^a   Firouzabadi, Habib ^a   Pourali, Ali Reza ^a  

^a SHIRAZ UNIVERSITY   (Iran)

Author keywords

Dinitrogen tetroxide; Disulfides; Oxidation; Thiols; Thiosulfonates

Indexed keywords

EID: 32944459314     PISSN: 10426507     EISSN: 15635325     Source Type: Journal    
DOI: 10.1080/10426500500263656     Document Type: Article

References (59)

1. (a) R. J. Cremlyn, An Introduction to Organosulfur Chemistry (John-Wiley & Sons, New York, 1996);
2. (b) S. Oae, Organic Sulfur Chemistry: Structure and Mechanism (CRC: Boca Raton, FL, 1991);
3. (c) B. Gaston, Biochim. Biophys. Acta, 1411, 323 (1999).
4. B. M. Trost, Chem. Rev., 78, 363 (1978);
5. (b) L. H. Fallois, J.-L. De'cout, and M. Fontecave, J. Chem. Soc., Perkin Trans. 1, 2587 (1997).
6. (a) A. R. Hajipour, S. E. Mallakpour, and H. Adibi, J. Org. Chem. 67, 8666 (2002);
7. (b) V. Kesavan, D. Bonnet-Delpon, and J. P. Begue, Synthetic Communication, 35, 1517 (2005);
8. (c) A. McKillop and D. Kuyuncu, A. Krief, W. Dumout, P. Reuiev, and M. Trabels, Tetrahedron Lett., 31, 5007 (1990);
9. (d) M. C. Noureldin, J. Hendry, and D. G. Lee, Synthesis, 1587 (1998).
10. (a) M. H. Ali and M. McDermott, Tetrahedron Lett., 43, 6271 (2002);
11. (b) X. Wu and R. D. Rieke, Synthetic Commun., 26, 191 (1996);
12. (c) J. Drabwicz and M. Mikolajczyk, Synthesis, 32 (1980).
13. (a) T. J. Wallace, J. Org. Chem., 31, 1217 (1966);
14. (b) H. Firouzabadi, N. Iranpoor, and H. A. Parham, Synthetic Commun., 14, 717 (1984);
15. (c) H. Firouzabadi, M. Naderi, A. Sardarian, and M. Vessal, Synthetic Commun., 13, 611 (1983);
16. (d) M. Tajbakhsh, I. Mohammadpoor-Baltork, and K. Alimohammadi, Monatsh. Chem., 134, 1571 (2003);
17. (e) M. M. Khodaei, I. Mohammadpoor-Baltork, and K. Nikoofar, Bull. Korean Chem. Soc., 24, 885 (2003);
18. (f) M. Tajbakhsh, R. Hosseinzadeh, and A. Shakoori, Tetrahedron Lett., 45, 1889 (2004).
19. F.-E. Chen, Y.-W. Lu, Y.-P. He, Y.-F. Luo, and M.-G. Yan, Synthetic Commun., 32, 3487 (2002).
20. R. Sanz, R. Aguado, M. R. Pedrosa, and F. J. Arna'iz, Synthesis, 856 (2002).
21. J. Kosmrlj, M. Kocevar, and S. Polanc, J. Chem. Soc., Perkin Trans. 1, 3917 (1998).
22. A. Cornelis, N. Depaye, A. Gerstmans, and P. Laszlo, Tetrahedron Lett., 24, 3103 (1983).
23. M. A. Zolfigol, Tetrahedron, 57, 9509 (2001).
24. L. Grossi, P. C. Montevecchi, and S. Strazzari, Eur. J. Org. Chem., 131 (2001).
25. G. A. Bagiyan, I. K. Koroleva, N. V. Soroka, and A. V. Ufimtsev, Russ. J. Appl. Chem., 76, 88 (2003).
26. (a) N. Iranpoor and B. Zeynizadeh, Synthesis, 49 (1999);
27. (b) B. Zeynizadeh and N. Iranpoor, J. Chin. Chem. Soc., 50, 849 (2003).
28. (a) K.-T. Liu and Y.-C. Tong, Synthesis, 669 (1978); and references therein,
29. (b) S. T. A. Shah, K. M. Khan, M. Fecker and W. Voelter, Tetrahedron Lett., 44, 6789 (2003);
30. M. M. Hashemi and Z. Karimi-Jaberi, Monatsh. Chem., 135, 41 (2004).
31. (a) N. Iranpoor, H. Firouzabadi, and M. A. Zolfigol, Synthetic Commun., 28, 367 (1998);
32. (b) N. Iranpoor, H. Firouzabadi, and M. A. Zolfigol, Synthetic Commun., 28, 1179 (1998).
33. H. Firouzabadi, A. Sardarian, and H. Badparva, Bull. Chem. Soc. Jpn., 69, 685 (1996).
34. (a) L. Grossi, P. C. Montevecchi, and S. Strazzari, J. Am. Chem. Soc., 123, 4853 (2001);
35. (b) W. A. Pryor, D. F. Church, C. K. Govindan, and G. Crank, J. Org. Chem., 47, 159 (1982).
36. (a) Y. H. Kim, K. Shinhama, D. Fukushima, and S. Oae, Tetrahedron Lett., 19, 1211 (1978);
37. (b) E. Bosch and J. K. Kochi, J. Org. Chem., 60, 3172 (1995).
38. (a) N. Iranpoor, H. Firouzabadi, and R. Heydari, J. Chem. Res. (S), 668 (1999);
39. (b) H. Firouzabadi, N. Iranpoor, and R. Heydari, Phosphorus, Sulfur, Silicon, Relat. Elem., 177, 631 (2002);
40. (c) H. Firouzabadi, N. Iranpoor, and R. Heydari, Synthetic Commun., 31, 2037 (2001);
41. (d) H. Firouzabadi, N. Iranpoor, and R. Heydari, Synthetic Commun., 33, 703 (2003);
42. (e) N. Iranpoor, H. Firouzabadi, and R. Heydari, Phosphorus, Sulfur, Silicon, Relat. Elem., 178, 1027 (2003);
43. (f) N. Iranpoor, H. Firouzabadi, and A. R. Pourali, Tetrahedron, 58, 5179 (2002);
44. (g) N. Iranpoor, H. Firouzabadi, and A. R. Pourali, Synthesis, 1591 (2003).
45. (a) N. Iranpoor, H. Firouzabadi, and A. R. Pourali, Synlett., 347 (2004);
46. (b) N. Iranpoor, H. Firouzabadi, and A. R. Pourali, Synthetic Commun., in press.
47. (a) J. P. Weidner and S. S. Block, J. Med. Chem., 7, 671 (1964);
48. (b) S. S. Block and J. P. Weidner, Mech. React. Sulfur Compd., 2, 235 (1968);
49. (c) N. S. Zefirof, N. V. Zyk, E. K. Beloglazkina, and A. G. Kutateladze, Sulfur Reports, 14, 223 (1993);
50. (d) K. Fujiki, S. H. Akieda, Yasuda, and Y. Sasaki, Synthesis, 1035 (2001).
51. G. Palumbo and R. Caputo, Synthesis, 888 (1981).
52. (a) T. F. Parsons, J. D. Buckman, D.E. Pearson, and L. Field, J. Org. Chem., 30, 1923 (1965);
53. (b) K. Fujiki, S. Akieda, H. Yasuda, and Y. Sasaki, Synthesis, 1035 (2001);
54. (c) K. Fujiki and E. Yoshida, Synthetic Commun., 29, 3289 (1999);
55. (d) G. Palumbo, C. Ferreri, C. D'Ambrocio, and R. Caputo, Phosphorus, Sulfur, Silicon, Relat. Elem., 19, 235 (1984) and references cited therein.
56. (a) M. Xia and Z.-C. Chen, Synthetic Commun., 27, 1301 (1997);
57. (b) J.-P. Mahieu, M. Gosselet, B. Sebille, and Y. Beuzard, Synthetic Commun., 16, 1709 (1986);
58. (c) N. Iranpoor, D. Mohajer, and A. R. Rezaeifard, Tetrahedron Lett. 45, 3811 (2004).
59. D. R. Lide, CRC Handbook of Chemistry and Physics, 80th ed, (CRC Press: Boca Raton, FL, 1999).