Oxidative coupling of thiols to disulfides with iodine in wet acetonitrile

Journal of Chemical Research - Part S

Volumn , Issue 11, 2002, Pages 564-566

  Zeynizadeh, Behzad ^a  

^a URMIA UNIVERSITY   (Iran)

Author keywords

Coupling; Disulfide; Iodine; Thiol

Indexed keywords

ACETONITRILE; DISULFIDE; IODINE; THIOL DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; OXIDATION; REACTION ANALYSIS; ROOM TEMPERATURE;

EID: 0036867075     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/030823402103170781     Document Type: Article

References (42)

1. (a) P.C. Jocelyn, Biochemistry of the Thiol Groups, Academic Press, New York, 1992. pp. 1;
2. (b) N. Kharasch and A.S. Arora, Phosphorous and Sulfur, 1976, 2, 1.
3. (a) G. Capozzi and G. Modena, The Chemistry of Thiol Group, Part 2, S. Patai, ed., Wiley, New York, 1974. pp. 785-839;
4. (b) N. Iranpoor and B. Zeynizadeh, Synthesis, 1999, 49.
5. (a) A. Cornelis and P. Laszalo, Synthesis, 1985, 909;
6. (b) S. Oae, D. Fukushima and Y.H. Kim, Chem. Commun., 1977, 407;
7. (c) T.L. Ho and C.M. Wong, J. Org. Chem. 1974, 39, 562;
8. (d) M. Huang and C.C. Chan, Synthesis, 1982, 1091.
9. A. McKillop and D. Koyuncu, Tetrahedron Lett., 1990, 31, 5010.
10. (a) H. Firouzabadi, N. Iranpoor, H. Parham, A. Sardarian and J. Toofan, Synth. Commun., 1984, 14, 717;
11. (b) H. Firouzabadi, N. Iranpoor, G. Hajipoor and J. Toofan, Synth. Commun., 1984, 14, 1033;
12. (c) H. Firouzabadi and I. Mohammadpour Baltork, Bull. Chem. Soc. Jpn., 1992, 65, 1131;
13. (d) H. Firouzabadi, N. Iranpoor, F. Kiaeezadeh and J. Toofan, Tetrahedron. 1986, 42, 719;
14. (e) H. Firouzabadi and N. Iranpoor, Synth. Commun., 1984, 14, 875;
15. (f) H. Firouzabadi, D. Mohager and M. Entezari-Moghadam, Bull. Chem. Soc. Jpn., 1988, 61, 2185.
16. A.M. Gasco, C. Medna and A. Gasco, Synth. Commun., 1994, 24, 2707.
17. K. Ramadas and N. Srinivasan, Synth. Commun., 1995, 25, 227.
18. A. Cornelis and P. Laszalo, Synlett, 1994, 155.
19. S.C. Askew, D.J. Barnett, J. McAninly and D.L.H. Williams, J. Chem. Soc., Perkin Trans. 2, 1995, 741.
20. D.J. Barnet, A. Rios and D.L.H. Williams, J. Chem. Soc., Perkin Trans. 2. 1995, 1279.
21. A.P. Dick, H.R. Swift, D.L.H. Williams, A.R. Butler, H.H. Al-Sadoni and B.G. Cox, J. Chem. Soc., Perkin Trans. 2, 1996, 481.
22. H.M. Meshram and R. Kache, Synth. Commun., 1997, 27, 2403.
23. M. Hirano, S. Yakabe, M. Fukami and T. Morimoto, Synth. Commun., 1997, 27, 2783.
24. N. Iranpoor, P. Salehi and F. Shiriny, J. Org. Prep. Proc. Inter., 1995, 27, 216.
25. H. Firouzabadi, N. Iranpoor and M.A. Zolfigol, Synth. Commun., 1998, 28, 1179.
26. G. Lu and Y. Zhang, Synth. Commun., 1998, 28, 4479.
27. N.A. Noureldin, M. Caldwell, J. Hendry and D.G. Lee, Synthesis. 1998, 1587.
28. (a) L.S. Sergio, V.L. Pardini and H. Viertler, Synth. Commun., 1990, 20, 393;
29. (b) F. Freeman, M.C. Keindl, N.P. Hendry, E. Brinkmas and J.A. Masse, Synthesis, 1989, 714.
30. (a) M. Sridhar, S. Kumaravedivel and V.T. Bhaelrao, Synth. Commun., 1998, 28, 1499;
31. (b) K.R. Rao and H.M.S. Kumar, Bioorg. Med. Chem. Lett., 1991, 1, 507.
32. V. Kesavan, D. Bonnet-Delpon and J.P. Begue, Synthesis. 2000, 223.
33. D.L. Small, J.H. Bailey and G.J. Cavallito. J. Am. Chem. Soc., 1947, 69, 1711.
34. T. Aida, T. Akasaka, N. Furukawa and S. Oae, Bull. Chem. Soc. Jpn., 1976, 49, 1441.
35. (a) J. Drabowicz and M. Mikolajczyk, Synthesis, 1980, 32;
36. (b) L.W. Christensen and D.J. Heacock, Synthesis, 1978, 50.
37. X. Wu, R.D. Rieke and L. Zhu, Synth. Commun., 1996, 26, 191.
38. G. Megnerian and L.B. Clapp, J. Am. Chem. Soc., 1951, 73, 486.
39. E.L. Colichman and D.L. Love, J. Am. Chem. Soc., 1953, 75, 5736.
40. T.M. Rogers and T.W. Campbell, J. Am. Chem. Soc., 1952, 74, 4742.
41. E.I. Tinyakova, E.K. Khrennidova and B.A. Dolgoplosk. Zhur. Obschei Khim., 1958, 28, 1632.
42. T. Sato, J. Otera and H. Nozaki, Tetrahedron Lett., 1990, 31, 3595.