Skip to main content
SpringerLink
Log in

Modified copolymers of bifunctional vinyl ethers with methyl vinyl sulfide as active matrices of solid superbases

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Reactive linear and crosslinked copolymers of diethylene glycol divinyl ether and ethylene glycol vinyl glycidyl ether with methyl vinyl sulfide have been synthesized in the presence of 2,2′-azobis(isobutyronitrile) (2%, 60 °C, 45–55 h) in ∼53% yield. The hydrolyzed at the residual vinyloxy and epoxy groups and oxidized at the methylthio groups copolymers upon treatment with KOH afford alkoxide (complex) and crown-like superbases. They are capable of catalyzing the acetone ethynylation, as well as the prototropic isomerization of methyl propargyl ether to allenyl methyl ether and vinylation of ethylene and diethylene glycols with acetylene.

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. B. A. Trofimov, Geteroatomnye proizvodnye atsetilena. Novye polifunktsional’nye monomery, reagenty i poluprodukty [Acetylene Heteroatomic Derivatives. New Polyfunctional Monomers, Reagents, and Intermediate Products], Nauka, Moscow, 1981, 319 pp. (in Russian).

    Google Scholar 

  2. N. A. Nedolya, Dr. Sci. Thesis, A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, 1998, 52 pp. (in Russian).

  3. B. A. Zhubanov, E. M. Shaikhutdinov, E. F. Osadchaya, Prostye vinilovye efiry v radikal’noi polimerizatsii [Vinyl Ethers in Radical Polymerization], Nauka, Alma-Ata, 1985, 155 pp. (in Russian).

    Google Scholar 

  4. B. A. Trofimov, L. V. Morozova, A. I. Mikhaleva, M. V. Markova, L. A. Oparina, T. Skotheim, Sulfur Lett., 2000, 23, 121.

    CAS  Google Scholar 

  5. L. N. Parshina, Dr. Sci. Thesis, A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, 2005, 341 pp. (in Russian).

  6. Pat. RF 1821474 (1990); Byul. Isobret. [Bull. Invent.], 1993, 22 (in Russian).

  7. A. A. Tager, M. V. Tsilipotkina, L. K. Kolmakova, E. V. Morozov, V. M. Balakin, T. S. Vydrina, E. V. Medvedeva, Vysokomolekulyar. Soedin., Ser. A, 1990, 32, 727 [Polym. Sci. USSR, Ser. A, 1990, 32 (Engl. Transl.)].

    CAS  Google Scholar 

  8. L. Ya. Tsarik, O. N. Novikov, V. V. Magdinets, J. Polymer Sci., Ser. A, 1996, 36, 371.

    Article  Google Scholar 

  9. M. Sangermano, G. Malucell, F. Morel, C. Decker, A. Priola, Eur. Polym. J., 1999, 35, 639.

    Article  CAS  Google Scholar 

  10. Z. S. Nurkeeva, G. A. Mun, V. V. Khutoryanskii, Vysokomolekulyar. Soedin., Ser. B, 2001, 43, 925 [Polym. Sci., Ser. B, 2001, 43 (Engl. Transl.)].

    CAS  Google Scholar 

  11. L. V. Morozova, I. V. Tatarinova, N. P. Kuznetsova, M. V. Markova, O. A. Tarasova, L. M. Sinegovskaya, T. I. Vakul’skaya, A. I. Mikhaleva, B. A. Trofimov, Izv. Akad. Nauk, Ser. Khim., 2006, 973 [Russ. Chem. Bull., Int. Ed., 2006, 55, 1010].

    Google Scholar 

  12. B. A. Trofimov, N. A. Nedolya, Reviews on Heteroatom Chem. (Jpn), 1993, 9, 205.

    CAS  Google Scholar 

  13. L. V. Morozova, T. T. Minakova, G. M. Tizenberg, I. G. Kuznetsov, M. G. Voronkov, B. A. Trofimov, Khim. Pharm. Zh., 1984, 1, 61 [Pharm. Chem. J., 1984 (Engl. Transl.)].

    Google Scholar 

  14. A. s. 1147719 SSSR; Byul. Isobret. [Bull. Invent.], 1985, 12 (in Russian).

  15. L. V. Morozova, A. I. Mikhaleva, I. P. Golentovskaya, L. P. Shaulina, B. A. Trofimov, Dokl. Akad. Nauk SSSR, 1992, 326, 835 [Dokl. Chem., 1992 (Engl. Transl.)].

    CAS  Google Scholar 

  16. Y. V. Mikhaylik, T. A. Skotheim, B. A. Trofimov, US Pat. 6569573 (2003); Chem. Abstrs, 2001, 134, 355483.

    Google Scholar 

  17. B. A. Trofimov, L. V. Morozova, M. V. Markova, A. I. Mikhaleva, G. F. Myachina, I. V. Tatarinova, T. A. Skotheim, Appl. Polym. Sci., 2006, 101, 4051.

    Article  CAS  Google Scholar 

  18. Pat. RF 2285557 (2005); Byul. Isobret. [Bull. Invent.], 2006, 29 (in Russian).

  19. V. V. Stepanov, A. R. Stepanova, S. S. Skorokhodov, V. I. Lavrov, B. A. Trofimov, Vysokomolekulyar. Soedin., Ser. A, 1986, 28, 2318 [Polym. Sci. USSR, Ser. A, 1986, 28 (Engl. Transl.)].

    CAS  Google Scholar 

  20. Atlas spektrov aromaticheskikh i geteroaromaticheskikh soedinenii. Vyp. 23. IK-spektry vinilovykh efirov, sul’fidov, sul’foksidov i KR-spektry arilvinilovykh efirov [Atlas of Spectra of Aromatic and Heteroaromatic Compounds. Issue. 23. IR Spectra of Vinyl Ethers, Sulfides, Sulfoxides, and CR spectra of Aryl Vinyl Ethers], Ed. V. A. Koptyug, Novosibirsk, 1982, 172 pp. (in Russian).

  21. A. Smith, Applied Infrared Spectroscopy, Wiley Intersci. Publ., New York, 1979.

    Google Scholar 

  22. B. A. Trofimov, Zh. Org. Khim., 1986, 22, 1991 [J. Org. Chem. USSR, 1986, 22 (Engl. Transl.)].

    CAS  Google Scholar 

  23. B. A. Trofimov, in Modern Problems of Organic Chemistry, VVM, St.-Petersburg, 2004, 14, 121.

    Google Scholar 

  24. B. A. Trofimov, N. K. Gusarova, Usp. Khim., 2007, 76, 550 [Russ. Chem. Rev., 2007, 76 (Engl. Transl.)].

    Google Scholar 

  25. B. A. Trofimov, L. V. Morozova, I. V. Tatarinova, A. I. Mikhaleva, O. V. Petrova, M. V. Markova, T. I. Vakul’skaya, Izv. Akad. Nauk, Ser. Khim., 2005, 774 [Russ. Chem. Bull., Int. Ed., 2005, 54, 789].

    Google Scholar 

  26. G. K. Musorin, S. V. Amosova, V. K. Stankevich, E. K. Andrievskaya, B. A. Trofimov, Zh. Prikl. Khim., 1987, 60, 2073 [J. Appl. Chem. USSR, 1987, 60 (Engl. Transl.)].

    CAS  Google Scholar 

  27. J. Rabek, Experimental Methods in Polymer Chemistry, Wiley and Sons, Chichester-New York-Brisbane-Toronto, 1980.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 ul. Favorskogo, 664033, Irkutsk, Russian Federation

    B. A. Trofimov, L. V. Morozova, A. I. Mikhaleva, M. V. Markova & I. V. Tatarinova

  2. Laboratory of Ammonia, BASF Corporation, M 311, 67056, Ludwigshafen, Germany

    J. Henkelmann

Authors
  1. B. A. Trofimov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. V. Morozova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. I. Mikhaleva
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. V. Markova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. I. V. Tatarinova
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. J. Henkelmann
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to B. A. Trofimov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2073–2077, October, 2008.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Trofimov, B.A., Morozova, L.V., Mikhaleva, A.I. et al. Modified copolymers of bifunctional vinyl ethers with methyl vinyl sulfide as active matrices of solid superbases. Russ Chem Bull 57, 2111–2116 (2008). https://doi.org/10.1007/s11172-008-0286-2

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-008-0286-2

Key words

Search

Navigation