An approach to disulfide synthesis promoted by sulfonyl chloride in sodium bicarbonate aqueous media

Phosphorus, Sulfur and Silicon and the Related Elements

Volumn 184, Issue 10, 2009, Pages 2553-2559

  Xiao, Huilong ^a   Chen, Jiuxi ^a   Liu, Miaochang ^a   Wu, Huayue ^a   Ding, Jinchang ^a  

^a WENZHOU UNIVERSITY   (China)

Author keywords

Aqueous media; Disulfides; Sulfonyl chloride

Indexed keywords

EID: 74849118312     PISSN: 10426507     EISSN: 15635325     Source Type: Journal    
DOI: 10.1080/10426500802529051     Document Type: Article

References (62)

1. (a) F. Freeman, M. Aregullin, and E. Rodriguez, Rev. Heteroat. Chem., 9, 1 (1993)
2. (b)Y. Kishi, S. Nakatsuga, T. Fukuyama, and M. Havel, J. Am. Chem. Soc., 95, 6493 (1973)
3. (c)S. Ito, A. Ota, H. Suhara, K. Tabashi, and Y. Kawashima, Chem. Pharm. Bull., 41, 1066(1993).
4. T. Mukaiyama and M. Hashimoto, J. Am. Chem. Soc., 94, 8528 (1972).
5. (a) T. Kondo and T. A. Mitsudo, Chem. Rev., 100, 3205 (2000)
6. (b)S. Kumar and L. Engman, J. Org. Chem., 71, 5400 (2006).
7. (a) K. Tanaka and K. Ajiki, Tetrahedron Lett., 45, 5677 (2004)
8. (b)R. D. Bach, O. Dmitrenko, and C. Thorpe, J. Org. Chem., 73, 12 (2008).
9. (a) J. Dowsland, F. McKerlie, and D. J. Procter, Tetrahedron Lett., 41, 4923 (2000)
10. (b)A. Z. Rys and D. N. Harpp, Tetrahedron Lett., 41, 7169 (2000).
11. (a) K. Hiroi, H. Miura, K. Kotsuji, and S. Sato, Chem. Lett., 10, 559 (1981)
12. (b)I. Nakagawa and T. Hata, Tetrahedron Lett., 16, 1409 (1975)
13. (c)G. A. Russell and S. V. Kulkarni, J. Org. Chem., 58, 2678 (1993)
14. (d)T. Mukaiyama, K. Goto, R. Matsueda, and M. Ueki, Tetrahedron Lett., 11, 5293 (1970).
15. T. Maddanimath, Y. B. Khollam, M. Aslam, I. S. Mulla, and K. Vijayamohanan, J. Power Sources, 124, 133 (2003).
16. (a) K. T. Liu and Y. C. Tong, Synthesis, 669 (1978)
17. (b)T. J. Wallace, J. Org. Chem., 31, 3071 (1966)
18. (c)T. Sato, J. Otera, and H. Nozaki, Tetrahedron Lett., 31, 3591 (1990)
19. (d)W. A. Pryor, D. F. Church, C. K. Govindan, and G. Crank, J. Org. Chem., 47, 156 (1982)
20. (e)J. R. Schaeffer, C. T. Goodhue, H. A. Risle, and R. E. Stevens, J. Org. Chem., 32, 392 (1967)
21. (f)J. Drabowicz and M. Mikolajczyk, Synthesis, 32 (1980)
22. (g)M. H. Ali and M. McDermott, Tetrahedron Lett., 43, 6271 (2002)
23. (h)T. Aida, T. Akasaka, N. Furukawa, and S. Oae, Bull. Chem. Soc. Jpn., 49, 1441 (1976)
24. (i) A. McKillop, D. Koyuncu, A. Krief, W. Dumont, P. Renier, and M. Trabelsi, Tetrahedron Lett., 31, 5007 (1990)
25. (j) J. Choi and N. M. Yoon, J. Org. Chem., 60, 3266 (1995)
26. (k) K. Ramadas and N. Srinivasan, Synth. Commun., 26, 4179 (1996)
27. (l) P. Salehi, A. Farrokhi, and M. Gholizadeh, Synth. Commun., 31, 2777 (2001)
28. (m) R.S.Varma, H. M. Meshram, and R. Dahiya, Synth. Commun., 30, 1249 (2000)
29. (n) N. A. Noureldin, M. Caldwell, J. Hendry, and D. G. Lee, Synthesis, 1587 (1998)
30. (o)B.J. Evans, J. T. Doi, and W. K. Musker, J. Org. Chem., 55, 2337 (1990)
31. (p) A. Shaabani and D. G. Lee, Tetrahedron Lett., 42, 5833 (2001)
32. (q) N. Iranpoor, H. Firouzabadi, and A. R. Pourali, Tetrahedron, 58, 5179 (2002)
33. (r) S. T. A. Shah, K. M. Khan, M. Fecker, and W. Volter, Tetrahedron Lett., 44, 6789 (2003)
34. (s) M. Tajbakhsh, R. Hosseinzadeh, and A. Shakoori, Tetrahedron Lett., 45, 1889 (2004)
35. (t) M. Carril, R. SanMartin, E. Dominguez, and I. Tellitu, Green Chem., 9, 315 (2007).
36. M. Arisawa, C. Sugata, and M. Yamaguchi, Tetrahedron Lett., 46, 6097 (2005).
37. S. C. Banfield, A.T. Omori, H. Leisch, and T. Hudlicky, J. Org. Chem., 72, 4989 (2007).
38. (a) N. Iranpoor and B. Zeynizadeh, Synthesis, 49 (1999)
39. (b) S. M. S. Chauhan, A. Kumar, and K. A. Srinivas, Chem. Commun., 2348 (2003)
40. (c) S. Patel and B. K. Mishra, Tetrahedron Lett., 45, 1371 (2004)
41. (d) M. Hashemi, H. Ghafuri, and Z. Karimi-Jaberi, J. Sulfur Chem., 27, 165 (2006)
42. (e) B. Karami, M. Montazerozohori, and M. H. Habibi, Molecules, 10, 1358 (2005).
43. (a)J.X.Chen, H. Y. Wu, C. Jin, X. X. Zhang, Y. Y. Xie, and W. K. Su, Green Chem., 8, 330 (2006)
44. (b) W. K. Su, J. X. Chen, H. Y. Wu, and C. Jin, J. Org. Chem., 72, 4524 (2007)
45. (c) W. K. Su, J. J. Li, Z. G. Zheng, and Y. C. Shen, Tetrahedron Lett., 46, 6037 (2005).
46. F. I. Ali, I. A. Hashmi, B. S. Siddiqui, and M. Rasheed, Synth. Commun., 37, 2461 (2007).
47. M. G. Ranasinghe and P. L. Fuchs, Synth. Commun., 18, 227 (1988).
48. (a) P. Kielbasinski, J. Drabowicz, and M. Mikolajczyk, J. Org. Chem., 47, 4806(1982)
49. (b)H. W. Pinnick, M. A Reynolds, R. T. Mcdonald Jr.,and W. D. Brewster, J. Org. Chem., 45, 930 (1980)
50. (c) N. B. Islam, H. Kwart, and S. Khan, J. Chem. Eng. Data, 30, 509 (1985)
51. (d) G. D. Figuly and J. C. Martin, J. Org. Chem., 45, 3728 (1980)
52. (e) S. Oae and H. Togo, Bull. Chem. Soc. Jpn., 56, 3813 (1983)
53. (f) S. Krishnamurthy and D. Aimino, J. Org. Chem., 54, 4458 (1989)
54. (g) R. Silvestri, G. De Le Martino, G. La Regina, M. Artico, S. Massa, L. Vargiu, M. Mura, A. G. Loi, T. Marceddu, and P. La Colla, J Med. Chem., 46, 2482 (2003)
55. (h) M. Montazerozohori, S. Joohari, B. Karami, and N. Haghighat, Molecules, 12, 694 (2007)
56. (i) B. Karami, M. Montazerozohori, and M. H. Habib, J Chem. Res., 8, 490 (2006)
57. (j) A. Onoue, M. Kawamura, T. Nishi, M. Yoshikawa, and Y. Lida, J.P. Patent, 62, 089, 655 A (1987)
58. (k) G. Crank and M. I. H. Makin, Tetrahedron Lett., 20, 2169 (1979)
59. (l) S. L. Colletti, J. R. Tata, H. C. Shen, F. X. Ding, J. L. Frie, J. E. Imbriglio, and W. C. Chen, W.O. Patent 2,006,057,922 A2 (2006)
60. (m) V. I. Cohen, Helv. Chim. Acta, 59, 840 (1976)
61. (n) J. E. Christian, G. L. Jenkins, L. C. Keagle, and J. A. Crum, J. Am. Pharm. AsSoc., 35, 328 (1946)
62. (o) A. R. Kiasat, B. Mokhtari, F. Kazemi, S. Yousefi, and M. Javaherian, J. Sulfur Chem., 28, 171 (2007).