Broønsted acidic ionic liquid 1-n-butylimidazolium tetrafluoroborate ([hbim]bf4): A green catalyst and recyclable medium for the azidolysis of epoxides

Journal of the Chemical Society of Pakistan

Volumn 34, Issue 3, 2012, Pages 593-598

  Heidarizadeh, Fariba ^a   Zarei, Amanolah ^a  

^a SHAHID CHAMRAN UNIVERSITY OF AHVAZ   (Iran)

Author keywords

2 Azidoalcohols; Azidolysis; Epoxide; Protic ionic liquid; Ring opening

Indexed keywords

EID: 84862211375     PISSN: 02535106     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (56)

1. S. Patai, Editor, The Chemistry of the Azido Group Wiley, NewYork, (1971).
2. S. E. F. V. Criven and K. Turnbull, Chemical Reviews, 88, 297 (1988).
3. G. A. Jacobs, J. A. Tino and R. Zahler, Tetrahedron Letters, 30, 6955 (1989).
4. D. M. Coe, P. L. Myers, D. M. Parry, S. M. Roberts and R. Storer, Chemical Communications, 151, (1990).
5. B. T. Smith, V. Gracias and J. Aube, Journal of the Organic Chemistry, 65, 3771 (2000).
6. J. G. Badiang and J. Aube, Journal of the Organic Chemistry, 61, 2484 (1996).
7. D. J. Ager, I. Prakash and D. Schaad, Chemical Reviews, 96, 835 (1996).
8. J. Takehara, S. Hashiguchi, A. Fujii, S. I. Inoue, T. Ikaria and R. Nayori, Chemical Communications, 233, (1996).
9. J. S. Yadav, B. V. S. Reddy, A. K. Basak and A. V. Narsaiah, Tetrahedron Letters, 44, 1047 (2003).
10. M. Liao, X. Duan, Y. Liang, Tetrahedron Letters, 46, 3469 (2005).
11. C. R. Brindaban, A. Laksmikanta and B. Subhash, Canadian Journal of Chemistry, 85, 366 (2007).
12. F. Heidarizadeh and A. Zarei, Asian Journal of Chemistry. 20, 1514 (2008).
13. T. L. Greaves and C. J. Drummond, Chemical Reviews, 108, 206 (2008).
14. M. A. B. H. Susan, A. Noda, S. Mitsushima and M. Watanabe, Chemical Communications, 938, (2003).
15. H. P. Zhu, F. Yang, J. Tang and M. Y. He, Green Chemistry, 5, 38 (2003).
16. H. H. Wu, F. Yang, P. Cui, J. Tang and M. Y. He, Tetrahedron Letters, 45, 4963 (2004).
17. G. Zhao, T. Jiang, H. Gao, B. Han, J. Huang and D. Sun, Green Chemistry, 6, 75 (2004).
18. A. R. Gholap, K. Venkatesan, T. Daniel, R. J. Lahoti and K. V. Srinivasan, Green Chemistry, 6, 147 (2004).
19. S. S. Palimkar, S. A. Siddiqui, T. Daniel, R. J. Lahoti and K. V. Srinivasan, Journal of the Organic Chemistry, 68, 9371 (2003).
20. For a discussion on the hazards associated with azides, see: Prudent Practice for Handling Hazardous Chemicals in Laboratories, National Academic Press, Washington, DC, pp. 87-88, (1983).
21. For human toxicity, see: N. J. Rahway, The Merck Index, Merck and Co, 12nd Edn pp. 4818 and 8726 (1996).
22. S. S. Palimkar, S. A. Siddiqui, T. Daniel, R. J. Lahoti and K. V. Srinivasan, Journal of the Organic Chemistry, 68, 9371 (2003).
23. S. Mallakpour and Z. Rafiee, Journal of Polymers and Environment 19, 447 (2011).
24. R. N. Nadaf, S. A. Siddiui, T. Daniel, R. J. Lahoti and K. V. Srinivasan, Journal of Molecular Catalysis A: Chemical, 214, 155 (2004).
25. A. R. Gholap, N. S. Chakor , T. Daniel, R. J. Lahoti and K. V. Srinivasan, Journal of Molecular Catalysis A: Chemical, 245, 37 (2006).
26. T. M. Potewar, S. A. Siddiqui, R. J. Lahoti and K. V. Srinivasan, Tetrahedron Letters, 48, 1721 (2007).
27. T. M. Potewar, R. J. Lahoti, D. Thomas and K. V. Srinivasan, Synthetic Communications, 37, 261 (2007).
28. T. M. Potewar, S. A. Ingale and K. V. Srinivasan, Synthetic Communications, 38, 3601 (2008).
29. R. G. Atul, S.C. Narayan, D. Thomas, J. L. Rajgopal and V. S. Kumar, Journal of Molecular Catalysis A: Chemical, 245, 37 (2006).
30. A. Aggarwal, N. L. Lancaster, A. R. Sethi and T. Welton, Green Chemistry, 4, 517 (2002).
31. Y. Danten, M. I. Cabaco and M. Besnard, Journal of Physical Chemistry A, 113, 2873 (2009).
32. X. Cui, S. Zhang, F. Shi, Q. Zhang, X. Ma, L. Lu and Y. Deng, ChemSusChem 3, 1043 (2010).
33. R. E. Mesmer and A. C Rutenberg, Inorganic Chemistry, 12, 699 (1973).
34. C. A. Wamser, Journal of American Chemical Society, 70, 1209 (1948).
35. M. G. Freire, C. M. S. S. Neves, M. Marrucho, J. A. P. Coutinho and A. M. Fernandes, Journal of Physical Chemistry A, 114, 3744 (2010).
36. S. Sebti, A. Solhy, R. Tahir, S. Boulaajaj, J. A. Mayoral, J. M.Fraile, A. Kossir, H. Oumimoun, Tetrahedron Letters, 42, 7953 (2001).
37. H. Firouzabadi, N. Iranpoor and B. Karimi, Synthetic Communications, 29, 2255 (1999).
38. B. Karimi, G. R. Ebrihimian and H. Seradj, Organic Letters, 1, 1737 (1999).
39. M. Barbasiewicz and M. Makosza, Organic Letters, 8, 3745 (2006).
40. N. Iranpoor and G. A. Kohmareh, Phosphorus, Sulfur, and Silicon and the Related Elements, 152, 135 (1999).
41. A. Olszewski, P. Gros and Y. Fort, Tetrahedron Letters, 38, 8699 (1997).
42. F. Benedetti, F. Berti and S. Norbedo, Tetrahedron Letters, 39, 7971 (1998).
43. F. Kazemi. A. R. Kiasat and S. Ebrahimi, Synthetic Communications, 33, 999 (2003).
44. G. Sabitha, R. S. Babu, M. Rajkumar and J. S. Yadav, Organic Letters, 4, 343 (2002).
45. A. R. Kiasat and M. Fallah-Mehrjardi, Journal of the Iranian Chemical Society, 6, 542 (2009).
46. A. R. Kiasat, R. Mirzajani, H. Shalbaf, T. Tabatabaei, M. Fallah-Mehrjardi, Journal of The Chinese Chemical Society 56, 594 (2009).
47. B. Yadollahi, H. Danafar, Catalalysis Letters, 113, 120 (2007).
48. A. R. Kiasat, R. Badri, B. Zargar and S. Sayyahi, Journal of the Organic Chemistry, 73, 8382 (2008).
49. A. R. Kiasat and M. Zayadi, Catalalysis Communications, 9, 2063 (2008).
50. B. Tamami, N. Iranpoor and R. Rezaie, Iranian Polymer Journal, 13, 495 (2004).
51. J. Boruwa, J. C. Borah, B. Kalita, N. C. Barua, Tetrahedron Letters, 45, 7355 (2004).
52. A. R. Kiasat and F. Kazemi, Phosphorus, Sulfur, and Silicon and the Related Elements, 178, 2387 (2003).
53. F. Fringuelli, O. Piermatti, F. Pizzo and L. Vaccaro, Journal of the Organic Chemistry, 64, 6094 (1999).
54. M. R. Sohrabi, A. Marjani, S. Moradi, M. D. Davallo and S. Shirazian, Journal of the Chemical Society of Pakistan, 33, 464 (2011).
55. L. Rishi, S. Jadoon, A. Waseem, M. Yaqoob, A. Journal of the Chemical Society of Pakistan, 33, 508 (2011).
56. D. H. He, J. T. Chen, Y. Y. Di, Z. P. Chen, D. Q. Wang and W. Y. Dan, Journal of the Chemical Society of Pakistan, 33, 333 (2011).