Trimethylchlorosilane (TMSCl) and cyanuric chloride (CC) catalyzed efficient oxidative coupling of thiols with dimethylsulfoxide

Synthesis

Volumn , Issue 17, 2002, Pages 2513-2516

  Karimi, Babak ^a   Hazarkhani, Hassan ^a   Zareyee, Daryoush ^a  

^a INSTITUTE FOR ADVANCED STUDIES IN BASIC SCIENCES IASBS   (Iran)

Author keywords

Disulfides; Oxidative coupling; Thiols

Indexed keywords

CATALYSIS; OXIDATION; SULFUR COMPOUNDS;

OXIDATIVE COUPLING;

CHLORINE COMPOUNDS;

CHLOROTRIMETHYLSILANE; CYANURIC ACID; CYANURIC CHLORIDE; DIMETHYL SULFOXIDE; DISULFIDE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CONCENTRATION RESPONSE; CRYSTALLIZATION; OXIDATION; REACTION ANALYSIS; STOICHIOMETRY; STRUCTURE ANALYSIS;

EID: 0036455008     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-35634     Document Type: Article

References (37)

1. Jocelyn, D. C. In Biochemistry of the Thiol Groups; Academic Press: New York, 1992.
2. Capozzi, G.; Modena, G. In The Chemistry of the Thiol Group; Patai, S., Ed.; Wiley: New York, 1974, PART 2, 785.
3. (a) Noureldin, M. C.; Hendry, J.; Lee, D. G. Synthesis 1998, 1587.
4. (b) Firouzabadi, H.; Abbassi, M.; Karimi, B. Synth. Commun. 1999, 29, 2527.
5. (c) Kesavan, V.; Bonnet-Delpon, D.; Begue, J. P. Synthesis 2000, 223.
6. (d) Fujihara, H.; Akashi, R.; Furukawa, N. Bull. Chem. Soc. Jpn. 1989, 62, 616.
7. (e) Meshram, H. M.; Kache, R. Synth. Commun. 1997, 27, 2403.
8. (f) Lu, G.; Zhang, Y. Synth. Commun. 1998, 28, 4479.
9. (g) McKillop, A.; Koyuneu, D. Tetrahedron Lett. 1990, 31, 5007.
10. (h) Karimi, B.; Zareyee, D. Synlett 2002, 346.
11. (a) Iranpoor, N.; Salehi, P.; Shiriny, F. Org. Prep. Proced. Int. 1995, 27, 216.
12. (b) Scrivens, G.; Gilbert, B. C.; Lee, C. P. T. J. Chem. Soc., Perkin Trans 2 1995, 995.
13. (c) Iranpoor, N.; Zeynizadeh, B. Synthesis 1999, 49.
14. (d) Iranpoor, N.; Firouzabadi, H.; Zolfigol, M. A. Synth. Commun. 1998, 28, 367.
15. (e) Raghavan, S.; Rajender, A.; Joseph, S. C.; Rasheed, M. A. Synth. Commun. 2001, 31, 1477.
16. (f) Choi, J.; Yoon, N. M. J. Org. Chem. 1995, 60, 3266.
17. (g) Arterburn, J. B.; Perry, M. C.; Nelson, S. L.; Dible, B. R.; Holguin, M. S. J. Am. Chem. Soc. 1997, 119, 9309.
18. (a) Yiannios, C. N.; Karabinos, J. V. J. Org. Chem. 1963, 28, 3246.
19. (b) Wallace, T. J. Chem. Ind (London) 1964, 501.
20. (c) Wallace, T. J. J. Am. Chem. Soc. 1964, 86, 2018.
21. (d) Wallace, T. J.; Mahon, J. J. J. Am. Chem. Soc. 1964, 86, 4099.
22. (e) Wallace, T. J.; Mahon, J. J. J. Org. Chem. 1965, 30, 1502.
23. (f) Wallace, T. J.; Weiss, H. A. Chem. Ind. (London) 1966, 1558.
24. Mancuso, A. J.; Swern, D. Synthesis 1981, 165.
25. Senier, A. Ber. 1886, 19, 311.
26. Venkataraman, K.; Wagle, D. R. Tetrahedron Lett. 1979, 3037.
27. Venkataraman, K.; Wagle, D. R. Tetrahedron Lett. 1980, 21, 1893.
28. Falorni, M.; Porcheddu, A.; Taddei, M. Tetrahedron Lett. 1999, 40, 4395.
29. Forbes, D. C.; Barrett, E. J.; Lewis, D. L.; Smith, M. C. Tetrahedron Lett. 2000, 41, 9943.
30. Manhas, M. S.; Bose, A. K.; Kajavi, M. S. Synthesis 1981, 209.
31. Olah, G. A.; Fung, A. P.; Gupta, B. G. B.; Narang, S. C. Synthesis 1980, 221.
32. De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2002, 4, 553; and references cited therein.
33. De Luca, L.; Giacomelli, G.; Porcheddu, A. J. Org. Chem. 2001, 66, 7907.
34. Groebel, W. Chem. Ber. 1960, 93, 284.
35. Cohen, V. I. Helv. Chim. Acta 1976, 59, 840.
36. Liu, K. T.; Tong, Y. C. Synthesis 1978, 669.
37. Ramadas, K.; Srinivasan, N. Synth. Commun. 1995, 25, 227.