Silphos [PCl3-n (SiO2)n]: A heterogeneous phosphine reagent for the regioselective synthesis of vic-haloalcohols

Phosphorus, Sulfur and Silicon and the Related Elements

Volumn 181, Issue 11, 2006, Pages 2615-2621

  Iranpoor, Nasser ^a   Firouzabadi, Habib ^a   Jamalian, Arezu ^a  

^a SHIRAZ UNIVERSITY   (Iran)

Author keywords

Epoxide; Heterogeneous phosphine; Molecular halogens; N halosuccinimide; Silphos; vic haloalcohol

Indexed keywords

EID: 33749164995     PISSN: 10426507     EISSN: 15635325     Source Type: Journal    
DOI: 10.1080/10426500600775989     Document Type: Article

References (36)

1. (a) A. McKillop and D. W. Young, Synthesis, 401, 481 (1979);
2. (b) G. Bram, E. d'Incan, and A. Loupy, Nouv. J. Chim., 6, 689 (1982);
3. P. Laszlo, Acc. Chem. Res., 19, 121 (1986);
4. J. H. Clark, A. P. Kybett, and D. J. Macquarrie, Supported Reagents: Preparation, Analysis, and Application (VCH, New York, 1992);
5. (e) K. Smith, Solid Supports and Catalysts in Organic Synthesis; (Ellis Horwood, Chichester, England, 1992);
6. (f) J. H. Clark, Catalysis of Organic Reactions by Supported Inorganic Reagents (VCH, New York, 1994);
7. (g) H. Kotsuki, T. Shimanouchi, R. Ohshima, and S. Fujiwara, Tetrahedron, 54, 2709 (1998).
8. R. S. Varma, Tetrahedron, 58, 1235 (2002).
9. (a) M. J. Hojo, Syn. Org. Chem. Jpn., 42, 635 (1984);
10. (b) K. Smith, Bull. Soc. Chim. Fr., 272 (1989);
11. T. Nishiguchi, J. Syn. Org. Chem. Jpn., 51, 308 (1993);
12. V. A. Basiuk, Russ. Chem. Rev., 64, 1003 (1995);
13. (e) A. K. Banerjee, M. S. Laya Mimó, and W. J. Vera Vegas, Russ. Chem. Rev., 11, 971 (2001).
14. (a) N. Iranpoor, H. Firouzabadi, A. Jamalian, and F. Kazemi, Tetrahedron, 61, 5699 (2005);
15. (b) N. Iranpoor, H. Firouzabadi, and A. Jamalian, Synlett, 1447 (2005);
16. N. Iranpoor, H. Firouzabadi, and A. Jamalian, Tetrahedron Lett., 46, 7963 (2005);
17. N. Iranpoor, H. Firouzabadi, and A. Jamalian, Tetrahedron, 62, 1823 (2006).
18. For some of the recent references, see (a) G. Smitha and C. S. Reddy, J. Chem. Res., 300 (2004);
19. (b) H. Sharghi, M. M. Eskandari, and R. Ghavami, J. Mol. Cat. A: Chemical, 215, 55 (2004);
20. H. Sharghi and M. M. Eskandari, Tetrahedron, 59, 8509 (2003);
21. K. Niknam and T. Nasehi, Tetrahedron, 58, 10259 (2002);
22. (e) H. Sharghi and M. M. Eskandari, Synthesis, 1519 (2002);
23. (f) B. Tamami and H. Mahdavi, Reactive and Functional Polymers, 51, 7 (2002);
24. (g) H. Sharghi, K. Niknam, and M. Pooyan, Tetrahedron, 57, 6057 (2001);
25. (h) W. H. Leung, T. K. T. Wong, J. C. H. Tran, and L. L. Yeung, Synlett, 677 (2000);
26. S. Munavalli, D. K. Rohrbaugh, D. I. Rossman, L. R. McMahon, and H. D. Durst, J. Organomet. Chem., 587, 160 (1999);
27. (j) R. Skupin and G. Haufe, J. Fluorine Chem., 92, 157 (1998).
28. (a) G. Palumbo, C. Ferreri, and R. Caputo, Tetrahedron Lett., 24, 1307 (1983);
29. (b) R. Caputo, C. Ferreri, S. Noviello, and G. Palumbo, Synthesis, 499 (1986);
30. D. Diaz, T. Martin, and V. S. Martin, J. Org. Chem., 66, 7231 (2001);
31. N. Iranpoor, H. Firouzabadi, and G. Aghapour, Synlett., 1176 (2001);
32. (e) F. Sartillo-Piscil, L. Quintero, C. Villegas, E. Santracruz- Juárez, and C. Anaya de Parrodi, Tetrahedron Lett., 43, 15 (2002);
33. (f) N. Iranpoor, H. Firouzabadi, G. Aghapour, and A. Nahid, Bull. Chem. Soc. Jpn., 77, 1 (2004).
34. G. Höefle, W. Steglich, and H. Vorbrüeggen, Angew. Chem. Int. Ed. Engl., 90, 569 (1978).
35. S. Trippet, J. Chem. Soc., 2337 (1962).
36. A. K. Bose and B. Lal, Tetrahedron Lett., 3937 (1973).