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Synthesis, characterization, and free radical polymerization of new acrylamide-based monomer containing a 1H-tetrazole ring: Thermal investigation and derivatization of the homopolymer

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Abstract

N-[4-(1H-Tetrazol-5-yloxy)phenyl]acrylamide was synthesized and subjected to homopolymerization under radical initiation. The structure of the monomer and homopolymer was characterized by elemental analyses (C, H, N), FT-IR, and 13C and 1H NMR data. Thermal behavior of the homopolymer was studied by differential scanning calorimetry and thermogravimetric analysis. The tetrazole ring in the homopolymer was converted into imidoyl azide derivatives via reactions with cyanogen bromide, p-toluenesulfonyl chloride, and trifluoro-methanesulfonyl chloride.

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References

  1. Finnegan, W.G., Henry, R.A., and Skolnik, S., US Patent no. 3004959; Chem. Abstr., 1962, vol. 56, p. 15518c.

    Google Scholar 

  2. Adicoff, A., US Patent no. 3036086; Chem. Abstr., 1962, vol. 57, p. 6147f.

    Google Scholar 

  3. Finnegan, W.G., Smith, R.L., and Wiebke, A.T., US Patent no. 3055780; Chem. Abstr., 1963, vol. 58, p. 407b.

    Google Scholar 

  4. Mishra, I.B. and Vande Kieft, L. J. Int Annu. Conf. ICT, 1988, vol. 25, p. 21; Chem. Abstr., 1989, vol. 111, no. 177417c.

    Google Scholar 

  5. Grasshoff, J.M. and Reid, J.L., US Patent no. 3936401; Chem. Abstr., 1976, vol. 84, no. 122 567v.

  6. Cieciuch, R.F.W., Luhowy, R.R., Meneghini, F.A., and Rogers, H.G., US Patent no. 4060417; Chem. Abstr., 1978, vol. 88, no. 81815m.

  7. Grasshoff, J.M. and Reid, J.L., US Patent no. 4134768; Chem. Abstr., 1979, vol. 90, no. 195583f.

  8. Stille, J.K. and Gotter, L.D., Macromolecules, 1969, vol. 2, p. 465.

    Article  CAS  Google Scholar 

  9. Stille, J.K. and Gotter, L.D., Macromolecules, 1969, vol. 2, p. 468.

    Article  CAS  Google Scholar 

  10. Stille, J.K. and Chen, A.T., Macromolecules, 1972, vol. 5, p. 377.

    Article  CAS  Google Scholar 

  11. Stille, J.K. and Chen, A.T., Polym. Prepr. (Am Chem. Soc., Div. Polym. Chem.), 1971, vol. 12, p. 1.

    CAS  Google Scholar 

  12. Kruglova, V.A., Annenkov, V.V., Vereshchagin, L.I., Pavlenko, V.V., Kazimirovskaya, V.B., Moskvitina, L.G., Boiko, N.M., Mansurova, L.A., Skornyakova, A.B., and Kalmykov, S.V., Khim.-Farm. Zh., 1987, vol. 21, p. 159.

    CAS  Google Scholar 

  13. Kruglova, V.A., Annenkov, V.V., Moskvilina, L.T., Boiko, N.M., Buzilova, S.R., Kazimirovskaya, V.B., Kizhnyaev, V.N., and Levina, M.N., Khim.-Farm. Zh., 1989, vol. 23, p. 195.

    CAS  Google Scholar 

  14. Annenkov, V.V., Kruglova, V.A., Kazimirovskaya, V.B., Leshchuk, S.L, Moskvitina, L.T., and Boiko, N.M., Khim.-Farm. Zh., 1995, vol. 29, p. 48.

    Google Scholar 

  15. Kizhnyaev, V.N., Smirnov, A.I., Biryukova, E.T., Novikov, V.I., and Aparin, P.G., Khim.-Farm. Zh., 1992, vol. 26, p. 55.

    Google Scholar 

  16. Annenkov, V.V. and Kruglova, V.A., Vyskomol. Soedin., Ser. A, 1991, vol. 33, p. 2050.

    CAS  Google Scholar 

  17. Kizhnyaev, V.N. and Kruglova, V.A., Zh. Prikl. Khim., 1992, vol. 65, p. 1879.

    CAS  Google Scholar 

  18. Wehman, T.C. and Popov, A.I., J. Phys. Chem., 1966, vol. 70, p. 3688.

    Article  CAS  Google Scholar 

  19. Duncia, J.V., Pierce, M.E., and Santella, J.B., III, J. Org. Chem., 1991, vol. 56, p. 2395.

    Article  CAS  Google Scholar 

  20. El-Ahl, A.-A.S., Elmorsy, S.S., Elbeheery, A.H., and Amer, F.A., Tetrahedron Lett., 1997, vol. 38, p. 1257.

    Article  CAS  Google Scholar 

  21. Zucchi, F., Trabanelli, G., and Fonsati, M., Corros. Sci., 1996, vol. 38, p. 2019.

    Article  CAS  Google Scholar 

  22. Cubreo, E., Orozco, M., and Luque, F.J., J. Am. Chem. Soc., 1998, vol. 120, p. 4723.

    Article  Google Scholar 

  23. Dabbagh, H.A. and Lwowski, W., J. Org. Chem., 1989, vol. 54, p. 3952.

    Article  CAS  Google Scholar 

  24. Dabbagh, H.A. and Gaelee, S., J. Org. Chem., 1996, vol. 61, p. 3439.

    Article  CAS  Google Scholar 

  25. Dabbagh, H.A. and Lwowski, W., J. Org. Chem., 2002, vol. 65, p. 7284.

    Article  CAS  Google Scholar 

  26. Dabbagh, H.A., Mansoori, Y., Jafary, M., and Rostami, M., J. Chem. Res., Synop., 2000, p. 442.

  27. Dabbagh, H.A. and Mansoori, Y., Dyes Pigm., 2002, vol. 54, p. 37.

    Article  CAS  Google Scholar 

  28. Taylor, E.C. and McKillop, A., Acc. Chem. Res., 1970, vol. 3, p. 338.

    Article  CAS  Google Scholar 

  29. Vollamr, A. and Hassner, A., J. Heterocycl. Chem., 1974, vol. 11, p. 491.

    Article  Google Scholar 

  30. Lioux, T., Gosselin, G., and Mathe, C., Eur. J. Org. Chem., 2003, p. 3997.

  31. Taden, A., Tait, A.H., and Kraft, A., J. Polym. Sci., Part A: Polym. Chem., 2002, vol. 40, p. 4333.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Isfahan University of Technology, Isfahan, 84156, Iran

    H. A. Dabbagh

  2. Department of Applied Chemistry, College of Science, University of Mohaghegh Ardabili, Ardabil, 56199-11367, Iran

    Y. Mansoori

Authors
  1. H. A. Dabbagh
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  2. Y. Mansoori
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Additional information

Published in Russian in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 6, pp. 890–897.

The text was submitted by the authors in English.

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Dabbagh, H.A., Mansoori, Y. Synthesis, characterization, and free radical polymerization of new acrylamide-based monomer containing a 1H-tetrazole ring: Thermal investigation and derivatization of the homopolymer. Russ J Org Chem 43, 888–896 (2007). https://doi.org/10.1134/S1070428007060152

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  • DOI: https://doi.org/10.1134/S1070428007060152

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