Skip to main content
SpringerLink
Log in

Generation of Perfluoro- and 1-Chloroperfluoro-Indanyl and -Benzocyclobutenyl Cations with Perfluoroalkyl Groups in the Aliphatic Ring

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Perfluoro(alkylbenzocycloalken-1-yl) cations were generated in a SbF5−SO2ClF medium from perfluorinated indane and benzocyclobutene derivatives containing perfluoroalkyl groups in the alicyclic fragment. The cations exist in equilibrium with their precursors. Adding SO2Cl2 to the system led to the formation of polyfluoroalkylbenzocycloalken-1-yl cations with a chlorine substituent at the cationic center. The structures of the cations were determined by 19F and 13C NMR spectroscopy and confirmed by the structures of perfluoroketones formed on their hydrolysis.

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. Karpov, V.M., Mezhenkova, T.V., Platonov, V.E., Sinyakov, V.R., and Shchegoleva, L.N., Russ. J. Org. Chem., 2002, vol.38, p.1158. doi https://doi.org/10.1023/A:1020901526459

    Article  CAS  Google Scholar 

  2. Karpov, V.M., Mezhenkova, T.V., Platonov, V.E., and Yakobson, G.G., J. Fluorine Chem., 1985, vol.28, p.121. doi https://doi.org/10.1016/S0022-1139(00)85198-2

    Article  CAS  Google Scholar 

  3. Karpov, V.M., Mezhenkova, T.V., Platonov, V.E., and Yakobson, G.G., Bull. Acad. Sci. USSR. Div. Chem. Sci., 1985, vol.34, p.2143. doi https://doi.org/10.1007/BF00963251

    Article  Google Scholar 

  4. Mezhenkova, T.V., Karpov, V.M., Beregovaya, I.V., Zonov, Ya.V., Chuikov, I.P., and Platonov, V.E., J. Fluorine Chem., 2016, vol.192, p.31. doi https://doi.org/10.1016/j.jfluchem.2016.10.009

    Article  CAS  Google Scholar 

  5. Olah, G.A. and Pittman, C.U., J. Am. Chem. Soc., 1966, vol.88, p.3310. doi https://doi.org/10.1021/ja00966a024

    Article  CAS  Google Scholar 

  6. Pozdnyakovich, Yu.V. and Shteingarts, V.D. J. Fluorine Chem., 1974, vol. 4, p. 283, p. 297. doihttps://doi.org/10.1016/S0022-1139(00)80865-9, doi https://doi.org/10.1016/S0022-1139(00)80866-0

    Article  CAS  Google Scholar 

  7. Beregovaya, I.V., Karpov, V.M., Mezhenkova, T.V., Platonov, V.E., and Chuikov, I.P., Russ. J. Org. Chem., 2012, vol.48, p.523. doi https://doi.org/10.1134/S1070428012040100

    Article  CAS  Google Scholar 

  8. Shtark, A.A., Pozdnyakovich, Yu.V., and Shteingarts, V.D., Zh. Org. Khim., 1977, vol.13, p.1671.

    CAS  Google Scholar 

  9. Galakhov, M.V., Belen’kii, G.G., Petrov, V.A., Fedin, E.I., and Bakhmutov, V.I., Bull. Acad. Sci. USSR Div. Chem. Sci., 1986, vol.35, p.956. doi https://doi.org/10.1007/BF00955357

    Google Scholar 

  10. Sheppard, W.A., J. Am. Chem. Soc., 1965, vol.87, p.2410. doi https://doi.org/10.1021/ja01089a020

    Article  CAS  Google Scholar 

  11. Yagupol’skii, L.M., Il’chenko, A.Ya., and Kondratenko, N.V., Russ. Chem. Rev., 1974, vol.43, p.32. doi https://doi.org/10.1070/RC1974v043n01ABEH001787

    Article  Google Scholar 

  12. Chambers, R.D., Fluorine in Organic Chemistry, Oxford: Blackwell Publishing, 2004. doi https://doi.org/10.1002/9781444305371

    Book  Google Scholar 

  13. Bondi, A., J. Phys. Chem., 1964, vol.68, p.441. doi https://doi.org/10.1021/j100785a001

    Article  CAS  Google Scholar 

  14. Mezhenkova, T.V., Karpov, V.M., Platonov, V.E., and Gatilov, Yu.V., J. Fluorine Chem., 2009, vol.130, p.951. doi https://doi.org/10.1016/j.jfluchem.2009.07.013

    Article  CAS  Google Scholar 

  15. Zonov, Ya.V., Karpov, V.M., Platonov, V.E., and Rybalova, T.V., J. Fluorine Chem., 2007, vol.128, p.1058. doi https://doi.org/10.1016/j.jfluchem.2007.05.020

    Article  CAS  Google Scholar 

  16. Zonov, Ya.V., Karpov, V.M., Platonov, V.E., and Rybalova, T.V., J. Fluorine Chem., 2013, vol.145, p.41. doi https://doi.org/10.1016/j.jfluchem.2012.11.004

    Article  CAS  Google Scholar 

  17. Karpov, V.M., Mezhenkova, T.V., Platonov, V.E., and Sinyakov, V.R., J. Fluorine Chem., 2002, vol.117, p.73. doi https://doi.org/10.1016/S0022-1139(02)00196-3

    Article  CAS  Google Scholar 

  18. Karpov, V.M., Mezhenkova, T.V., Platonov, V.E., and Yakobson, G.G., J. Fluorine Chem., 1985, vol.28, p.115. doi https://doi.org/10.1016/S0022-1139(00)85197-0

    Article  CAS  Google Scholar 

  19. Karpov, V.M., Mezhenkova, T.V., and Platonov, V.E., Russ. Chem. Bull., 1992, vol.41, p.1110. doi https://doi.org/10.1007/BF00866598

    Article  Google Scholar 

  20. Karpov, V.M., Mezhenkova, T.V., and Platonov, V.E., Russ. Chem. Bull., 1990, vol.39, p.566. doi https://doi.org/10.1007/BF00959585

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090, Russia

    T. V. Mezhenkova, V. M. Karpov, Ya. V. Zonov & I. P. Chuikov

  2. Novosibirsk State University, ul. Pirogova 1, Novosibirsk, 630090, Russia

    Ya. V. Zonov

Authors
  1. T. V. Mezhenkova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. M. Karpov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ya. V. Zonov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. I. P. Chuikov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to T. V. Mezhenkova.

Additional information

Russian Text © T.V. Mezhenkova, V.M. Karpov, Ya.V. Zonov, I.P. Chuikov, 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 2, pp. 242–251.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mezhenkova, T.V., Karpov, V.M., Zonov, Y.V. et al. Generation of Perfluoro- and 1-Chloroperfluoro-Indanyl and -Benzocyclobutenyl Cations with Perfluoroalkyl Groups in the Aliphatic Ring. Russ J Org Chem 55, 193–201 (2019). https://doi.org/10.1134/S1070428019020118

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428019020118

Keywords

Search

Navigation