BiCl3 catalyzed thiolyzation reaction of 1,2-epoxides with diaryl disulfides in the presence of zinc powder and ionic liquid

Phosphorus, Sulfur and Silicon and the Related Elements

Volumn 180, Issue 11, 2005, Pages 2525-2531

  Khosropour, A R ^a   Khodaei, M M ^a   Ghozati, K ^a  

^a RAZI UNIVERSITY   (Iran)

Author keywords

hydroxysulfides; Aryl disulfides; BiCl3; Epoxides; Ionic liquid; Ring opening reaction

Indexed keywords

EID: 31744451625     PISSN: 10426507     EISSN: 15635325     Source Type: Journal    
DOI: 10.1080/104265090929931     Document Type: Article

References (33)

1. (a) C. G. Aifheli and P. T. Kaye, Synth. Commun. 26, 4459 (1996);
2. (b) H. Sugihara, H. Mabuchi, M. Hirata, T. Iamamoto, and Y. Kawamatsu. Chem. Pharm. Bull., 35, 1930 (1987).
3. M. A. Adger, J. B. Barkley, S. Bergeron, M. W. Cappi, B. E. Floweden, M. P. Jackson, R. McCange, T. C. Nugent, and S. M. Roberts. J. Chem. Soc. Perkin Trans., 1, 3501 (1997).
4. (a) C. Gabbi, F. Ghelgi and R. Grandi. Synth. Commun., 27, 2857 (1997);
5. (b) C. Alvarez-Ibarra, R. Cuervo-Rodriguez, M. C. Fernanedz-Monreal, and M. P. Ruiz. J. Org. Chem., 59, 7287 (1994).
6. J.-P. Bégué, D. Monnet-Delpon, and A. Kornilov. Synthesis 529 (1996).
7. G. Capozzi and G. Modena, The Chemistry of the Thiol Group (John Wiley, New York, 1974).
8. (a) F. Fringuelli, F. Pizzo, S. Tortoioli, and L. Vaccaro. Green Chem., 5, 436 (2003);
9. (b) C. Alan, A. C. Spivey, R. Srikaran, C. M. Diaper, J. David, and D. Turner. J. Org. Biomol. Chem., 1, 1638 (2003);
10. (c) F. Fringuelli, F. Pizzo, S. Tortoioli, and L. Vaccaro. Tetrahedron Lett., 44, 6785 (2003);
11. (d) D. Amantini, F. Fringuelli, F. Pizzo, S. Tortoioli, and L. Vaccaro. Synthesis, 2292 (2003);
12. (e) J. S. Yadav, B. V. S. Reddy, and G. Baishya. Chem. Lett., 906 (2002).
13. (a) T. Welton, Chem. Rev., 99, 2071 (1999);
14. (b) P. Wasserscheid and W. Keim, Angew. Chem. Int. Ed., 39, 3772 (2000).
15. (a) B. Ganchegui, S. Bouquillon, F. Henin, and J. Muzart, Tetrahedron Lett., 43, 6641 (2002);
16. (b) B. C. Ranu, A. Das, and S. Samanta, J. Chem. Soc., Perkin Trans., 1, 1520 (2002);
17. (c) K. Selvakumar, A. Zapt, and M. Beller, Org. Lett., 4, 3031 (2002).
18. (a) J. R. Harjani, S. J. Nara, and M. M. Salunkhe, Tetrahedron Lett., 43, 1127 (2002);
19. (b) V. V. Namboodiri and R. S. Varma, Chem. Commun., 342 (2002);
20. (c) R. Sheldon, Chem. Commun., 2399 (2001).
21. (a) S. Cunha, B. R. Lima, and A. R. Souza. Tetrahedron Lett., 43, 49 (2002);
22. (b) S. Cunha, B. R. Lima, and A. R. Souza. Tetrahedron Lett., 43, 49 (2002);
23. (c) G. Sabitha, E. V. Reddy, R. Swapna, N. M. Reddy, and J. S. Yaddav, Synlett., 1276 (2004).
24. T. Ollevier and G. Lavie-Compin, Tetrahedron Lett., 45, 49 (2004).
25. (a) I. Mohammadpoor-Baltork and A. R. Khosropour, Monatsh. Chem., 133, 189 (2002);
26. (b) I. Mohammadpoor-Baltork, A. R. Khosropour, and H. Alian. J. Chem. Res. (S), 280 (2001);
27. (c) I. Mohammadpoor-Baltork, H. Alian, and A. R. Khosropour. Tetrahedron, 57, 5851 (2001);
28. (d) M. M. Khodaei, A. R. Khosropour, and K. Ghozati. Tetrahedron Lett., 45, 3525 (2004).
29. (e) M. M. Khodaei, A. R. Khosropour, and S. J. Hoseini Jomor. J. Chem. Res. (S), 10, 638 (2003);
30. (f) A. R. Khosropour, M. M. Khodaei, and K. Ghozati. Chem. Lett., 33, 304 (2004);
31. (g) A. R. Khosropour, M. M. Khodaei, and M. Khookhazadeh. Tetrahedron Lett., 45, 1725 (2004).
32. (a) H. Firouzabadi, N. Iranpoor, and M. A. Zolfigol, Synth. Commun., 28, 1179 (1998);
33. (b) A. R. Hajipour and S. E. Mallakpour, J. Chem. Research (S), 32 (2000).