Skip to main content
SpringerLink
Log in

New unsymmetrical difluoroaromatic compounds and estimation of their reactivities in nucleophilic substitution

  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

A series of previously unknown unsymmetrical difluoroaromatic compounds, viz., p-fluorobenzoylphenyl(p-fluorophenyl)-substituted imidazoles, pyrazines, and quinoxalines, were synthesized according to multistep procedures with the use of chloral as the key compound. The reactivities of the resulting difluoroaromatic compounds were estimated based on 19F and 13C NMR spectral data and the results of quantum-chemical calculations. The calculated charge densities on the Cipso atoms correlate linearly with the experimental chemical shifts in the 19F and 13C NMR spectra. Difluoroaromatic compounds, which are characterized by δF > –110 and δC > 163 and by the charge density on the Cipso atom higher than 0.08 e, are sufficiently activated to be used for the preparation of high-molecular-weight polyethers.

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. A. L. Rusanov, G. B. Sarkisyan, and M. L. Keshtov, Vysokomol. Soedin., 1999, 41, 27 [Polym. Sci., Ser. A, 1999, 41 (Engl. Transl.)].

    Google Scholar 

  2. P. Hergenrother, J. Connel, J. Labadie, and L. Hedrick, Adv. Polym. Sci.,1994, 117, 68.

    Google Scholar 

  3. R. Singh and A. Hay, Macromolecules, 1991, 24, 2637.

    Google Scholar 

  4. P. Horner and R. Whitelay, J. Mat. Chem., 1991, 1, 1397.

    Google Scholar 

  5. F. Mercer, M. Mckenze, G. Mevlino, and M. Fone, J. Appl. Polym. Sci., 1995, 56, 1397.

    Google Scholar 

  6. J. E. Douglas and Y. Wang Zhi, Macromolecules, 1995, 28, 5970.

    Google Scholar 

  7. Y. K. Han, S. D. Chi, and Y. H. Kim, Macromolecules, 1995, 28, 916.

    Google Scholar 

  8. J. Douglas and Y. Wang Zhi, Macromol. Chem. Phys., Rapid Commun., 1996, 17, 795.

    Google Scholar 

  9. A. L. Rusanov, Prog. Polym. Sci., 1994, 19,589.

    Google Scholar 

  10. M. L. Keshtov, A. L. Rusanov, N. M. Belomoina, T. M. Kazieva, and A. K. Mikitaev, Izv. Akad. Nauk, Ser. Khim., 1996, 670 [Russ. Chem. Bull., 1996, 45, 630 (Engl. Transl.)].

    Google Scholar 

  11. F. A. Gunter and R. C. Blinn, J. Chem. Educ., 1950, 27, 654.

    Google Scholar 

  12. E. D. Chattaway and R. J. Muir, J. Chem. Soc., 1934, 701.

  13. H. L. Bradlow and C. A. van der Werf, J. Am. Chem. Soc., 1947, 69, 662.

    Google Scholar 

  14. K. Sonogoshira and S. Takahashi, J. Synt. Org. Chem. Jpn., 1993, 51, 1053.

    Google Scholar 

  15. N. M. Belomoina, Ph. D. (Chem.) Thesis, A. N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, Moscow, 1978, 164 pp. (in Russian).

  16. K. R. Carter, R. D. Miller, and J. Hedric, Macromolecules, 1993, 26, 2209.

    Google Scholar 

  17. K. R. Carter, Macromolecules, 1995, 28, 6462.

    Google Scholar 

  18. J. Hedrick and K. R. Carter, Macromolecules, 1995, 28, 4340.

    Google Scholar 

  19. A. Lozano, L. Jimeno, J. Abajo, and J. Campa, Macromolecules, 1994, 27, 7164.

    Google Scholar 

  20. J. Hedrick, R. Twieg, T. Matray, and K. Carter, Macromolecules, 1993, 26, 4833.

    Google Scholar 

  21. M. L. Keshtov, A. R. Khokhlov, G. B. Sarkisyan, N. M. Belomoina, and A. L. Rusanov, V Europ. Tech. Symp. on Polyimides "High Performance Functional Polymers" (3-5 May, 1999), Abstrs., Montpellier (France), 1999, CIII-5.

Download references

Author information

Authors and Affiliations

  1. Russian Academy of Sciences, A. N. Nesmeyanov Institute of Organoelement Compounds, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    M. L. Keshtov, A. L. Rusanov & P. V. Petrovskii

  2. Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 119899, Moscow, Russian Federation

    S. V. Keshtova

  3. Russian Academy of Sciences, N. M. Emanuel" Institute of Biochemical Physics, 4 ul. Kosygina, 119991, Moscow, Russian Federation

    A. A. Shchegolikhin

Authors
  1. M. L. Keshtov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. L. Rusanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. V. Keshtova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. P. V. Petrovskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. A. Shchegolikhin
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Keshtov, M.L., Rusanov, A.L., Keshtova, S.V. et al. New unsymmetrical difluoroaromatic compounds and estimation of their reactivities in nucleophilic substitution. Russian Chemical Bulletin 51, 117–123 (2002). https://doi.org/10.1023/A:1015022032506

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1015022032506

Search

Navigation