Petroleum Chemistry

, Volume 59, Supplement 1, pp S88–S94 | Cite as

Cage Polycyclic Hydrocarbons Based on Adducts of Norbornadiene-2,5 and Anthracene Derivatives

  • S. V. Shorunov
  • M. A. Rudakova
  • M. E. Fil’kina
  • Yu. V. Nelyubina
  • M. V. BermeshevEmail author


Double adducts of norbornadiene-2,5 and anthracene derivatives have been synthesized using the Diels–Alder reaction. The possibility of selective preparation of both symmetrical and unsymmetrical adducts depending on the reaction conditions has been shown. For these cycloadducts exclusively consisting of carbon and hydrogen, an unusual and interesting feature has been revealed, namely, the signals of the protons of the bridge methylene groups in the 1H NMR spectra have chemical shifts in the negative region. In this work, double adducts of anthracene derivatives and norbornadiene (2,5-(bicyclo-[2.2.1]-hepta-2,5-diene)) have been synthesized and their structure investigated. The synthesized compounds possess a rigid, branched, and bulky structure suitable for the fabrication of composite membrane materials.


norbornadiene anthracene cycloaddition cage hydrocarbons NMR spectroscopy 



The authors are grateful to the “Biospectrotomography” shared-use center of the Moscow State University for the use of an NMR spectrometer. X-ray diffraction studies were supported by the Ministry of Science and Higher Education of the Russian Federation with the use of the scientific equipment of the Center for Molecular Structure Investigation of the Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences.


This work was performed as part of a state task for the Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences.


The authors declare no conflict of interest to be disclosed in this work.


  1. 1.
    L. M. Robeson, J. Membr. Sci. 320, 390 (2008).CrossRefGoogle Scholar
  2. 2.
    Y. Yampolskii, Macromolecules 45, 3298 (2012).CrossRefGoogle Scholar
  3. 3.
    J. Ahn, W. J. Chung, I. Pinnau, and M. D. Guiver, J. Membr. Sci. 314, 123 (2008).CrossRefGoogle Scholar
  4. 4.
    D. S. Bakhtin, L. A. Kulikov, S. A. Legkov, et al., J. Membr. Sci. 554, 211 (2018).CrossRefGoogle Scholar
  5. 5.
    P. P. Chapala, M. V. Bermeshev, L. E. Starannikova, et al., J. Membr. Sci. 474, 83 (2015).CrossRefGoogle Scholar
  6. 6.
    P. P. Chapala, M. V. Bermeshev, L. E. Starannikova, et al., Polym. Compos. 36, 1029 (2015).CrossRefGoogle Scholar
  7. 7.
    A. F. Bushell, P. M. Budd, M. P. Attfield, et al., Angew. Chem., Int. Ed. Engl. 52, 1253 (2013).CrossRefGoogle Scholar
  8. 8.
    R. G. D. Taylor, M. Carta, C. G. Bezzu, et al., Org. Lett. 16, 1848 (2014).CrossRefGoogle Scholar
  9. 9.
    M. L. Gringol’ts, M. V. Bermeshev, A. V. Syromolotov, et al. Pet. Chem. 50, 352 (2010).CrossRefGoogle Scholar
  10. 10.
    M. L. Gringolts, M. V. Bermeshev, Y. V. Nelyubina, and E. S. Finkelshtein, Pet. Chem. 49, 369 (2009).CrossRefGoogle Scholar
  11. 11.
    B.-G. Kang, D.-G. Kim, and R. A. Register, Macromolecules 51, 3702 (2018).CrossRefGoogle Scholar
  12. 12.
    M. V. Bermeshev and P. P. Chapala, Prog. Polym. Sci. 84, 1 (2018).CrossRefGoogle Scholar
  13. 13.
    E. V. Bermesheva, D. A. Alentiev, A. P. Moskalets, and M. V. Bermeshev, Polym. Sci., Ser. B 61, 314 (2019).CrossRefGoogle Scholar
  14. 14.
    D. A. Alentiev, E. S. Egorova, M. V. Bermeshev, et al., J. Mater. Chem. A 6, 19393 (2018).CrossRefGoogle Scholar
  15. 15.
    L. J. Bourhis, O. V. Dolomanov, R. J. Gildea, et al., Acta Crystallogr., Sect. A 71, 59 (2015).CrossRefGoogle Scholar
  16. 16.
    J. Cui, J.-X. Yang, L. Pan, and Y.-S. Li, Macromol. Chem. Phys. 217, 2708 (2016).CrossRefGoogle Scholar
  17. 17.
    D. N. Butler, A. Barrette, and R. A. Snow, Synth. Commun. 5, 101 (1975).CrossRefGoogle Scholar
  18. 18.
    T. Sasaki, K. Kanematsu, I. Ando, and O. Yamashita, J. Am. Chem. Soc. 99, 871 (1977).CrossRefGoogle Scholar
  19. 19.
    M. N. Paddon-Row and R. Hartcher, J. Am. Chem. Soc. 102, 671 (1980).CrossRefGoogle Scholar
  20. 20.
    M. Hong, L. Cui, S. Liu, and Y. Li, Macromolecules 45, 5397 (2012).CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • S. V. Shorunov
    • 1
  • M. A. Rudakova
    • 1
    • 2
  • M. E. Fil’kina
    • 1
  • Yu. V. Nelyubina
    • 3
  • M. V. Bermeshev
    • 1
    • 2
    Email author
  1. 1.Topchiev Institute of Petrochemical Synthesis, Russian Academy of SciencesMoscowRussia
  2. 2.Mendeleev University of Chemical Technology of RussiaMoscowRussia
  3. 3.Nesmeyanov Institute of Organoelement Compounds, Russian Academy of SciencesMoscowRussia

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