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Radical Copolymerization of N-Substituted 2-Azanorborn-5-enes with N-Vinylpyrrolidone

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Abstract

The radical copolymerization of N-methyl-2-azanorborn-5-ene, N-benzyl-2-azanorborn-5-ene, N-allyl-2-azanorborn-5-ene, and N-(2-azanorborn-5-en-2-yl)methyl acetate with N-vinylpyrrolidone is carried out in bulk in the presence of AIBN as an initiator. It is shown that the copolymerization yields statistical copolymers enriched in N-vinylpyrrolidone units. It is demonstrated that the rate of copolymerization decreases with increasing fraction of azanorbornene in the initial monomer mixture. Using 13С NMR spectroscopy, it is found that the copolymerization of azanorbornenes with N-vinylpyrrolidone occurs via the double bond of the norbornene ring. The allyl group of N-allyl-2-azanorborn-5-ene is uninvolved in copolymerization at both the equimolar comonomer ratio and the double excess of N-vinylpyrrolidone.

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REFERENCES

  1. I. Minoru, M. Atsushi, and K. Nobuya, Heterocycles 58, 317 (2002).

    Article  Google Scholar 

  2. C. H. Mitch and S. J. Quimby, US Patent No. 6559171, Ref. Zh., Khim. No. 23, 19O.161P (2003).

  3. D. M. Hodgson, C. R. Maxwell, R. Wisedale, I. R. Matthews, K. J. Carpenter, A. H. Dickenson, and S. Wonnacott, J. Chem. Soc., Perkin Trans. 1, No. 23, 3150 (2001).

  4. C. D. Cox, J. R. Malpass, J. Gordon, and A. Rosen, J. Chem. Soc., Perkin Trans. 1, No. 19, 2372 (2001).

  5. K. Schiemann and J. Leibrock, DE Patent No. 10044905, Ref. Zh., Khim. No. 22, 19O.57P (2002).

  6. T. Fukumoto and R. Ikarashi, EP Patent No. 1048650, Ref. Zh., Khim., No. 7, 19N.136P (2001).

  7. V. Perrin, V. Riveron, G. Balme, and J. Gore, J. Chem. Res., Synop., No. 2, 60 (2000).

    Article  Google Scholar 

  8. D. M. Hadgson, C. R. Maxwell, and I. R. Matthews, Synlett, No. 12, P. 1349 (1998).

  9. J. R. Malpass and C. D. Cox, Tetrahedron Lett. 40, 1419 (1999).

    Article  CAS  Google Scholar 

  10. H. Sunden, I. Ibrahem, L. Eriksson, and A. Cordova, Angew. Chem., Int. Ed. 44, 4877 (2005).

    Article  CAS  Google Scholar 

  11. A. A. Ruggiu, R. Lysek, E. Moreno-Clavijo, A. J. Moreno-Vargas, I. Robina, and P. Vogel, Tetrahedron 66, 7309 (2010).

    Article  CAS  Google Scholar 

  12. E. Wojaczynska, J. Wojaczyński, K. Kleniewska, M. Dorsz, and T. K. Olszewski, Org. Biomol. Chem. 13, 6116 (2015).

    Article  CAS  Google Scholar 

  13. V. Dragutan and R. Streck, Catalytic Polymerization of Cycloolefins: Ionic, Ziegler-Natta and Ring-Opening Metathesis Polymerization (Elsevier, Amsterdam, 2000).

    Google Scholar 

  14. G. Berger, L. Fusaro, M. Luhmer, A. der Lee, B. Crousse, and F. Meyer, Tetrahedron Lett. 55, 6339 (2014).

    Article  CAS  Google Scholar 

  15. E. Rossegger, L. Oláh, R. Fischer, P. Kaschnitz, O. Varga, M. Kallay, G. Scheipl, F. Stelzer, and F. Wiesbrock, Polym. Chem. 3, 2760 (2012).

    Article  CAS  Google Scholar 

  16. A. I. Vorob’eva, M. N. Gorbunova, V. D. Surkov, R. R. Muslukhov, F. A. Sataeva, S. V. Kolesov, A. G. Tolstikov, and Yu. B. Monakov, Russ. J. Appl. Chem. 80, 1712 (2007).

    Article  Google Scholar 

  17. M. N. Gorbunova, Russ. J. Appl. Chem. 83, 1429 (2010).

    Article  CAS  Google Scholar 

  18. S. D. Larsen and P. A. Grieco, J. Am. Chem. Soc. 107, 1768 (1985).

    Article  CAS  Google Scholar 

  19. A. Gordon, and R. Ford, The Chemist’s Companion, A Handbook of Practical Data. Techniques and References (Wiley, New York, 1972).

    Google Scholar 

  20. A. M. Toroptseva, K. V. Belogorodskaya, and V. M. Bondarenko, Laboratory Manual for Chemistry and Engineering of Polymers (Khimiya, Leningrad, 1972) [in Russian].

    Google Scholar 

  21. F. R. Mayo and F. J. Lewis, J. Am. Chem. Soc. 66, 1594 (1944).

    Article  CAS  Google Scholar 

  22. M. Finemann and S. D. Ross, J. Polym. Sci. 5, 269 (1950).

    Article  Google Scholar 

  23. T. Kelen and F. Tüdős, J. Macromol. Sci., Chem. 9, 27 (1975).

    Article  Google Scholar 

  24. G. B. Levy and H. P. Frank, J. Polym. Sci. 17 (84), 247 (1955).

    Article  CAS  Google Scholar 

  25. P. Clerk and S. Simon, in Spectral Data for Structure Determination of Organic Compounds, Ed. by E. Pretsch, P. Bühlmann, and M. Badertscher (Springer-Verlag, Berlin, 1983), p. 380.

    Google Scholar 

  26. G. A. Olah, A. M. White, J. R. DeMember, A. Commeyras, and C. Y. Liu, J. Am. Chem. Soc. 92, 4627 (1970).

    Article  CAS  Google Scholar 

  27. D. R. Arnold, D. J. Trecker, and E. B. Whipple, J. Am. Chem. Soc. 87, 2596 (1965).

    Article  CAS  Google Scholar 

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Funding

This work was supported by the Russian Foundation for Basic Research (project no. 19-43-590019-r_ural-a).

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Authors and Affiliations

  1. Institute of Technical Chemistry, Ural Branch, Russian Academy of Sciences, 614013, Perm, Russia

    M. N. Gorbunova & I. A. Borisova

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  1. M. N. Gorbunova
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  2. I. A. Borisova
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Correspondence to M. N. Gorbunova.

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Translated by T. Soboleva

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Gorbunova, M.N., Borisova, I.A. Radical Copolymerization of N-Substituted 2-Azanorborn-5-enes with N-Vinylpyrrolidone. Polym. Sci. Ser. B 62, 30–38 (2020). https://doi.org/10.1134/S1560090420010029

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  • DOI: https://doi.org/10.1134/S1560090420010029

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