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An efficient catalyst-free ring opening of epoxides in peg-300: A versatile method for the synthesis of vicinal azidoalcohols

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Abstract

Efficient and regioselective conversion of epoxides to 1,2-azidoalcohols has been carried out by treatment of sodium azide using polyethylene glycol as the reaction medium. The reaction afforded the corresponding products with high regioselectivity under mild reaction conditions.

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References

  1. B.T. Cho, S.K. Kang, S.H. Shin, Tetrahedron Asymmetry 13 (2002) 1209.

    CAS  Google Scholar 

  2. S.J. Gorzynski, Synthesis (1984) 629.

    Google Scholar 

  3. E.F.V. Scriven, K. Turnbull, Chem. Rev. 88 (1988) 297.

    CAS  Google Scholar 

  4. D.M. Coe, P.L. Myers, D.M. Parry, S.M. Roberts, R.J. Storer, J. Chem. Soc., Chem. Commun. (1990) 151.

    Google Scholar 

  5. B.T. Smith, V. Gracias, J.J. Aube, Org. Chem. 65 (2000) 3771.

    CAS  Google Scholar 

  6. J.G. Badiang, J.J. Aube, Org. Chem. 61 (1996) 2484.

    CAS  Google Scholar 

  7. S. Patai, The Chemistry of the Azido Group Ed., Wiley, New York, 1971.

  8. H.B. Mereyala, B. Frei, Helv. Chim. Acta 69 (1986) 415.

    CAS  Google Scholar 

  9. M. Onaka, K. Sugita, Y.J. Izumi, Org. Chem. 54 (1989) 1116.

    CAS  Google Scholar 

  10. S. Saito, S. Yamashita, T. Nishikawa, Y. Yokoyama, M. Inaba, T. Moriwake, Tetrahedron Lett. 30 (1989) 4153.

    CAS  Google Scholar 

  11. S. Saito, T. Nishikawa, Y. Yokoyama, T. Mariwake, Tetrahedron Lett. 31 (1990) 221.

    CAS  Google Scholar 

  12. M. Chini, P. Crotti, F. Macchia, Tetrahedron Lett. 31 (1990) 5641.

    CAS  Google Scholar 

  13. M. Hayashi, K. Kohmura, N. Oguni, Synlett (1991) 774.

    Google Scholar 

  14. K.B. Hansen, J.L. Leighton, E.N. Jacobsen, J. Am. Chem. Soc. 118 (1996) 10924.

    CAS  Google Scholar 

  15. P. Crotti, V.D. Bussolo, L. Favero, F. Macchia, M. Pineschi, Tetrahedron Lett. 37 (1996) 1675.

    CAS  Google Scholar 

  16. F. Benedetti, F. Berti, S. Norbedo, Tetrahedron Lett. 39 (1998) 7971.

    CAS  Google Scholar 

  17. N. Iranpoor, F. Kazemi, Synthetic Commun. 29 (1999) 561.

    CAS  Google Scholar 

  18. A. Kamal, M. Arifuddin, M.V. Rao, Tetrahedron Asymmetry 10 (1999) 4261.

    CAS  Google Scholar 

  19. B. Tamami, H. Mahdavi, Tetrahedron Lett. 42 (2001) 8721.

    CAS  Google Scholar 

  20. J.H.L. Spelberg, J.E.T.H. Vlieg, L. Tang, D.B. Janssen, R.M. Kellogg, Org. Lett. 3 (2001) 41.

    CAS  Google Scholar 

  21. G. Sabitha, R.S. Babu, M. Rajkumar, J.S. Yadav, Org. Lett. 4 (2002) 343.

    CAS  Google Scholar 

  22. G. Sabitha, R.S. Babu, M.S.K. Reddy, J.S. Yadav, Synthesis 15 (2002) 2254.

    Google Scholar 

  23. F. Kazemi, A.R. Kiasat, S. Ebrahimi, Synth. Commun. 33 (2003) 999.

    CAS  Google Scholar 

  24. B. Tamami, N. Iranpoor, R. Rezaie, Iran. Polym. J. 13 (2004) 495.

    CAS  Google Scholar 

  25. B. Tamami, M. Kolahdoozan, H. Mahdavi, Iran. Polym. J. 13 (2004) 21.

    CAS  Google Scholar 

  26. S.-W. Chen, S.S. Thakur, W. Li, C.-K. Shin, R.B. Kawthekar, G.-J. Kim, J. Mol. Catal. A-Chem. 259 (2006) 116.

    CAS  Google Scholar 

  27. B. Yadollahi, H. Danafar, Catal. Lett. 113 (2007) 120.

    CAS  Google Scholar 

  28. A. Sharifi, M.S. Abaee, M. Mirzaei, R. Salimi, J. Iran. Chem. Soc. 5 (2008) 135.

    Article  CAS  Google Scholar 

  29. S. Campestrini, G. Lora, U. Tonellato, Tetrahedron Lett. 42 (2001) 7045.

    CAS  Google Scholar 

  30. S. Chandrasekhar, C. Narsihmulu, G. Chandrashekar, T. Shyamsunder, Tetrahedron Lett. 45 (2004) 2421.

    CAS  Google Scholar 

  31. S.Y. Wang, S.J. Ji, Synth. Commun. 38 (2008) 1291.

    CAS  Google Scholar 

  32. E. Santaniello, A. Manzocchi, P. Sozzani, Tetrahedron Lett. 20 (1979) 4581.

    Google Scholar 

  33. F. Benedetti, F. Berti, S. Norbedo, Tetrahedron Lett. 39 (1998) 7971.

    CAS  Google Scholar 

  34. F. Fringuelli, O. Piermatti, F. Pizzo, L.J. Vaccaro, Org. Chem. 64 (1999) 6094.

    CAS  Google Scholar 

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Authors and Affiliations

  1. Chemistry Department, Faculty of Sciences, Shahid Chamran University, Ahvaz, 61357-4-3169, Iran

    A. R. Kiasat & M. Fallah-Mehrjardi

Authors
  1. A. R. Kiasat
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  2. M. Fallah-Mehrjardi
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Correspondence to A. R. Kiasat.

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Kiasat, A.R., Fallah-Mehrjardi, M. An efficient catalyst-free ring opening of epoxides in peg-300: A versatile method for the synthesis of vicinal azidoalcohols. JICS 6, 542–546 (2009). https://doi.org/10.1007/BF03246533

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  • DOI: https://doi.org/10.1007/BF03246533

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