The green method for regiospecific ring opening of epoxide with dimercaptoethane

Phosphorus, Sulfur and Silicon and the Related Elements

Volumn 182, Issue 8, 2007, Pages 1709-1716

  Seyedi, Seyed Mohammad ^a   Sadeghian, Hamid ^a   Rezai, Masoomeh ^a  

^a FERDOWSI UNIVERSITY OF MASHHAD   (Iran)

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EID: 34250897378     PISSN: 10426507     EISSN: 15635325     Source Type: Journal    
DOI: 10.1080/10426500701313888     Document Type: Article

References (39)

1. (a) S. Garzynski, Synthesis, 1984, 629;
2. (b) C. Bonini and G. Righi, Synthesis, 1994, 225;
3. (c) W. M. Dai, J. Wu, and A. Wu, Tetrahedron Lett., 1998, 39, 4091;
4. (d) I. C. González and C. J. forsyth, Tetrahedron Lett., 2000, 41, 8805;
5. (e) O. A. Ozhogina, Tetrahedron Lett., 2002, 43, 553;
6. (f) K. Surendra, N. S. Krishnaveni, Y. V. D. Nageswar, and K. R. Rao, J. Org. Chem., 2003, 68, 4994;
7. (g) A. Solladié-Cavallo, P. Lupattelli, and C. Bonini, J. Org. Chem., 2005, 70, 1605;
8. (h) R. M. Jong, J. J. W. Tiesinga, A. Villa, L. Tang, D. B. Janssen, and B. W. Dijkstra, J. Am. Chem. Soc., 2005, 127, 13338.
9. (a) E. J. Corey, D. A. Clark, G. Goto, A. Marfat, C. Mioskowski, B. Samuelsson, and S. Hammarstorm, J. Am. Chem. Soc., 1980, 102, 1436;
10. (b) M. F. Sebban, P. Vottero, A. Alagui, and G. Dupuy, Tetrahedron Lett., 2000, 41, 1019;
11. (c) S. Patai, Ed., The Chemistry of The Thiol Group, (John Wiley, New York, 1974).
12. A. E. Vougiokas and H. B. Kagan, Tetrahedron Lett., 1987, 28, 6065.
13. J. Iqbal, A. Pandey, A. Shukla, R. R. Srivastava, and S. Tripathi, Tetrahedron, 1990, 46, 6423.
14. (a) S. Y. Ko and K. B. Sharpless, J. Org. Chem., 1986, 51, 5413;
15. (b) Y. Belokon, M. Flego, N. Ikonnikov, M. Moscalenko, and M. North, Tetrahedron Asymm., 1996, 7, 851;
16. (c) Y. Jiang, L. Gong, X. Feng, and W. Hu, Tetrahedron, 1997, 53, 14327;
17. (d) J. Wu, X. L. Hou, L. J. Xia and M. H. Tang, Tetrahedron Asymm., 1998, 9, 3431.
18. (a) R. M. Hanson and K. B. Sharpless, J. Org. Chem., 1986, 51, 1922;
19. (b) K. Narasaka, N. Iwasawa, M. Inoue, T. Yamada, and M. Nakashima. J. Am. Chem. Soc., 1989, 111, 5340.
20. (c) K. Mikami, M. Terada, and T. Nakai, J. Am. Chem. Soc., 1990, 112, 3949;
21. (d) H. Sasai, T. Arai, Y. Satow, K. N. Houk, and M. Shibasaki, J. Am. Chem. Soc., 1995, 117, 6194;
22. (e) T. Arai, Y. M. A. Yamada, N. Yamamoto, H. Sasai, and M. Shibasaki, Chem. Eur. J., 1996, 2, 1368;
23. (f) T. Aria, H. Sasai, K. Aoe, K. Okamura, and M. Shibasaki, Angew. Chem. Int. Ed. Engl., 1996, 35, 104.
24. (a) D. Amantini, F. Fringuelli, F. Pizzo, S. Tortoioli, and L. Vaccaro, Synlett, 2003, 15, 2292;
25. (b) F. Fringuelli, F. Pizzo, S. Tortoioli, and L. Vaccaro, J. Org. Chem., 2003, 68, 8248.
26. F. Fringuelli, F. Pizzo, S. Tortoioli, and L. Vaccaro, Adv. Synth. Catal., 2002, 344, 379.
27. (a) G. H. Posmer and O. Z. Rogers, J. Am. Chem. Soc., 1977, 99, 8208;
28. (b) A. S. Rao, S. K. Paknihar and J. G. Kirtane, Tetrahedron, 1983, 39, 2323.
29. A. K. Maiti and P. Behattacharyya, Tetrahedron, 1994, 50, 10483.
30. V. Kesavan, D. Bennet-Delpar, and P. J. Bégue, Tetrahedron Lett., 2000, 41, 2895.
31. M. R. Younes, M. M. Chaabouni, and A. Baklouti, Tetrahedron Lett., 2001, 42, 3167.
32. J. Chen, H. Wu, C. Jin, X. Zhang, Y. Xie, and W. Su, Green Chem., 2006, 8, 330.
33. (a) V. Guyon, A. Guy, J. Foos, M. Lemaire, and M. Draye, Tetrahedron, 51, 4065 (1995);
34. (b) G. W. Gokel, W. M. Leevy, and E. M. Weber, Chem. Rev., 104, 2723 (2004).
35. P. T. Anastas, Ed., Green Chemistry: Challenging Perspective, Oxford Se. Pub., Oxford, 1999.
36. V. Pironti and S. Colonna, Green. Chem., 2005, 7, 43.
37. F. A. Carey and R. J. Sundberg, Advanced Organic Chemistry, (Kluwer Academic/Plenum Pub., New York, 2000), 4th. ed., Vol. 1, Chap. 5, pp. 263-295.
38. E. Stahl, Ed., Thin-Layer Chromatography (Springer-Verlag Berlin, Heidelberg, New York, 1969), 2nd ed., Chap. Z, p. 885.
39. J. H. Clark, Green Chem., 2006, 8, 17.