Skip to main content
SpringerLink
Log in

Nucleophilic substitution reactions using Polyacrylamide-Based phase transfer catalyst in organic and aqueous media

  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

Poly [N-(2-aminoethyl) acrylamido] trimemethyl ammonium chloride was prepared and used as an effective heterogeneous phase-transfer catalyst. This modified polyacrylamide catalyzed nucleophilic displacement of alkyl halides for easy preparation of alkyl thiocyanates, alkyl cyanides, alkyl azides, and alkyl aryl ethers in high yields and short reaction times in organic and aqueous media under two-phase and triphase conditions. The catalyst can be recovered and reused several times.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. W.E. Keller, Phase Transfer Reaction, Georg Thieme: Stuttgart, Vol. 3 (1992) Fluka-Compendium.

    Google Scholar 

  2. a) E.V. Dehmlow & S.S. Dehmlow, Phase transfer catalysis (3rd ed.) (1993), Weinheim, Germany: Verlag Chemie

    Google Scholar 

  3. M.E. Halpern, (Ed.). ACS symposium series 659: Phase-transfer catalysis, mechanisms and syntheses, Washington D.C., U.S.A: American Chemical Society, (1997)

    Google Scholar 

  4. S.D. Naik, and L.K. Doraiswamy, Phase transfer catalysis: Chemistry and engineering. A.I.Ch.E. Journal, 44(3) (1998) 612.

    CAS  Google Scholar 

  5. Y. Sasson, R. Neumann, Handbook of Phase Transfer Catalysis, first ed. Blackie Academic & Professional, London, UK, (1997) 1.

    Book  Google Scholar 

  6. C.M. Starks, C.L. Liotta & M. Halpern, Phase Transfer Catalysis, Fundamentals, Applications, and Industrial Perspectives, Chapman & Hall Inc., New York, (1994).

    Google Scholar 

  7. a) S.L. Regen, Angew. Chem., Int. Ed. Engl. 18 (1979) 421

    Google Scholar 

  8. M. Tomoi, W.T. Ford, In Synthesis and Separation Using Functional Polymers, Sherrington, D. C.; Hodge, P. Eds. Wiley: New York, (1988) 181.

    Google Scholar 

  9. S. Kondo, T. Murayama, Y. Takeda & K. Tsuda, Makromol. Chem. Rapid Commun. 9 (1988) 625.

    CAS  Google Scholar 

  10. M.S. Chiles, D.D. Jackson, Reeves, P. C. J. Org. Chem. 45 (1980) 2915.

    CAS  Google Scholar 

  11. M.S. Chiles, P.C. Reeves, Tetrahedron Lett. 36 (1979) 3367.

    Google Scholar 

  12. K. Aiswaryakumari, K. Sreekumar, J. Appl. Polym Sci. 59 (1996) 2039.

    Google Scholar 

  13. S.L. Regen, A. Mehrotra & A. Singh, J. Org. Chem. 46 (1981) 2183.

    Google Scholar 

  14. V. Janout, P. Cefelin, Tetrahedron Lett. 27 (1986) 3525.

    CAS  Google Scholar 

  15. C.M. Starks, J. Am. Chem. Soc. 93 (1971) 195.

    CAS  Google Scholar 

  16. a) A.A. Newman, Chemistry and Biochemistry of Thiocyanic Acid and its Derivatives, 1st ed.; Academic Press: New York, (1975)

    Google Scholar 

  17. B.W. Leblanc, B.S. Jursic, Synth. Commun. 28 (1988) 3591.

    Google Scholar 

  18. S. Kondo, T. Okamura, M. Takesue, H. Kunisada & Y. Yuki, Makromol. Chem. 193 (1992) 2265.

    CAS  Google Scholar 

  19. S. Kondo, T. Yamamoto, M. mase, H. Kunisada & Y. Yuki, J. Polym. Sci. 30 (1992) 1535.

    CAS  Google Scholar 

  20. M. Kodomari, T. Kuzuoka & S. Yoshitomi, synthesis (1983) 141.

    Google Scholar 

  21. S. Kondo, M. Nakanishi & K. Tsuda, J. Polym. Sci. Polym. Chem. Ed. 23 (1985) 581.

    CAS  Google Scholar 

  22. a) S. Kondo, T. Okamura, M. Takesue, H. Kunisada & Y. Yuki, Makromol. Chem. 193 (1992) 2265.

    CAS  Google Scholar 

  23. D. Landini, A. Maia, F. Montanari, and F. Rolla, J. Org. Chem. 48 (1983) 3774.

    CAS  Google Scholar 

  24. M. Tomoi, and W.T. Ford, J. Am. Chem. Soc. 102 (1980) 7140.

    CAS  Google Scholar 

  25. G. Manecke, A. Kramer, Makromol. Chem., 182 (1981) 3017.

    CAS  Google Scholar 

  26. S. Kondo, T. Okamura, M. Takesue, H. Kunisada & Y. Yuki, Makromol. Chem. 193 (1992) 2265.

    CAS  Google Scholar 

  27. H. Lehmkuhl, F. Rabet & K. Hauschild, Synthesis (1977) 184.

    Google Scholar 

  28. R.S. Varma, K.P. Naicker & D. Kumar, J. Mol. Catal. 149 (1999) 153.

    CAS  Google Scholar 

  29. S.L. Regen, A. Mehrotra, and A. Singh, J. Org. Chem. 46 (1981) 2182.

    CAS  Google Scholar 

  30. W.M. Mackenzie, and D.C. Sherrington, Polymer 21 (1980) 791.

    CAS  Google Scholar 

  31. W.M. Mackenzie, and D.C. Sherrington, Polymer 22 (1981) 431.

    CAS  Google Scholar 

  32. S. Kondo, T. Yamamoto, M. mase, H. Kunisada & Y. Yuki, J. Polym. Sci. 30 (1992) 1535.

    CAS  Google Scholar 

  33. L. Li, J. Shi, J. Yan, H. Chen & X. Zhao, J. Mol. Catal.: Chemical 209 (2004) 227.

    CAS  Google Scholar 

  34. a) C. Li, J. Chem. Rev. 93 (1993) 2023

    CAS  Google Scholar 

  35. T.H. Chan, C.J. Li, Can. J. Chem. 72 (1994) 1181

    CAS  Google Scholar 

  36. A. Lubineau, J. Auge & Y. Queneau, Synthesis (1994) 741.

    Google Scholar 

  37. a) B. Tamami, H. Mahdavi, React. Func. Polym. 51 (2002) 7

    CAS  Google Scholar 

  38. B. Tamami, H. Mahdavi, Phosphorus, Sulfur and Silicon 180 (2005) 1929

    Google Scholar 

  39. a) B. Tamami, M. Kolahdoozan, Tetrahedron Lett. 45 (2004) 1535

    CAS  Google Scholar 

  40. B. Tamami, A.H. Fadavi, Catalysis Communication 6 (2005) 747.

    CAS  Google Scholar 

  41. S.L. Regen, J. Am. Chem. Soc. 97 (1975) 5956

    CAS  Google Scholar 

  42. S.L. Regen, J. Org. Chem. 42 (1977) 875.

    CAS  Google Scholar 

  43. M. Cinouni, S. Colonna, H. Molinari, and F. Montanari, J. Chem. Soc. Chem. Comm. (1976) 394.

    Google Scholar 

  44. R. Fornasier and F. Montanari, Tetrahedron Lett. 17 (1976) 1381.

    Google Scholar 

  45. P. Tundo, P. Venturello, J. Am. Chem. Soc. 101 (1979) 6606.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Shiraz University, Shiraz, Iran

    B. Tamami & S. Ghasemi

Authors
  1. B. Tamami
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. Ghasemi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to B. Tamami.

Additional information

Dedicated to my dear friend and colleague Professor H. Forouzabadi on the occasion of his 65th birthday

Rights and permissions

Reprints and permissions

About this article

Cite this article

Tamami, B., Ghasemi, S. Nucleophilic substitution reactions using Polyacrylamide-Based phase transfer catalyst in organic and aqueous media. JICS 5 (Suppl 1), S26–S32 (2008). https://doi.org/10.1007/BF03246485

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF03246485

Key words

Search

Navigation