SpringerLink
Log in

Opening of the four-membered ring in perfluorinated 1-alkyl-2-phenyl- and 1-aryl-1,2-dihydrocyclobutabenzenes in the system I2-SbF5

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

Abstract

Reactions of perfluorinated 1-phenyl-, 1-(2-ethylphenyl)-, 1-(4-ethylphenyl)-, 1-methyl-2-phenyl-, and 1-ethyl-2-phenyl-1,2-dihydrocyclobutabenzenes with iodine in antimony pentafluoride at 130°C, followed by hydroysis of the reaction mixture, resulted in the formation of perfluorinated 2-methyl-, 2-ethyl-2′-methyl-, 4-ethyl-2′-methyl-, 2-ethyl-, and 2-propylbenzophenones via opening of the four-membered ring in the initial cyclobutabenzene at the C1–C2 bond. The presence of hydrogen fluoride facilitates the process and promotes profound transformations leading to anthracene derivatives.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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., and Yakobson, G.G., Bull. Soc. Chim. Fr., 1986, p. 980.

  2. Karpov, V.M., Mezhenkova, T.V., and Platonov, V.E., J. Fluorine Chem., 1996, vol. 77, p. 133.

    Article  CAS  Google Scholar 

  3. Karpov, V.M., Mezhenkova, T.V., Platonov, V.E., and Shchegoleva, L.N., Izv. Akad. Nauk SSSR, Ser. Khim., 1991, p. 2618.

  4. Karpov, V.M., Mezhenkova, T.V., and Platonov, V.E., Mendeleev Commun., 1997, p. 71.

  5. Mezhenkova, T.V., Karpov, V.M., and Platonov, V.E., Russ. J. Org. Chem., 2010, vol. 46, p. 1418.

    Article  CAS  Google Scholar 

  6. 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.

    Article  CAS  Google Scholar 

  7. Karpov, V.M., Mezhenkova, T.V., Platonov, V.E., and Sinyakov, V.R., J. Fluorine Chem., 2002, vol. 117, p. 73.

    Article  CAS  Google Scholar 

  8. Sinyakov, V.R., Mezhenkova, T.V., Karpov, V.M., Platonov, V.E., Rybalova, T.V., and Gatilov, Yu.V., Russ. J. Org. Chem., 2003, vol. 39, p. 837.

    Article  CAS  Google Scholar 

  9. Mezhenkova, T.V., Karpov, V.M., and Platonov, V.E., Russ. J. Org. Chem., 2011, vol. 47, p. 1018.

    Google Scholar 

  10. Sinyakov, V.R., Mezhenkova, T.V., Karpov, V.M., and Platonov, V.E., Russ. J. Org. Chem., 2007, vol. 43, p. 1677.

    Article  CAS  Google Scholar 

  11. Kemmitt, R.D.W., Murray, M., McRae, V.M., Peacock, R.D., Symons, M.C.R., and O’Donnell, T.A., J. Chem. Soc. A, 1968, p. 862; Davies, C.G., Gillespie, R.J., Ireland, P.R., and Sowa, J.M., Can. J. Chem., 1974, vol. 52, p. 2048.

  12. Morozov, A.V. and Maksimov, B.N., Fluorine Notes, 2009, no. 6 (67).

  13. Pozdnyakovich, Yu.V. and Shteingarts, V.D., J. Fluorine Chem., 1974, vol. 4, p. 283.

    Article  CAS  Google Scholar 

  14. Pozdnyakovich, Yu.V. and Shteingarts, V.D., J. Fluorine Chem., 1974, vol. 4, p. 297.

    Article  Google Scholar 

  15. Mezhenkova, T.V., Sinyakov, V.R., Karpov, V.M., Platonov, V.E., and Gatilov, Yu.V., J. Fluorine Chem., 2009, vol. 130, p. 951.

    Article  CAS  Google Scholar 

  16. Karpov, V.M., Mezhenkova, T.V., Platonov, V.E., and Sinyakov, V.R., J. Fluorine Chem., 2001, vol. 107, p. 53.

    Article  CAS  Google Scholar 

  17. Gutowsky, H.S. and Mochel, V.D., J. Chem. Phys., 1964, vol. 39, p. 1195.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

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

    T. V. Mezhenkova, V. M. Karpov & V. E. Platonov

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. V. E. Platonov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to T. V. Mezhenkova.

Additional information

Original Russian Text © T.V. Mezhenkova, V.M. Karpov, V.E. Platonov, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 7, pp. 1012–1019.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Mezhenkova, T.V., Karpov, V.M. & Platonov, V.E. Opening of the four-membered ring in perfluorinated 1-alkyl-2-phenyl- and 1-aryl-1,2-dihydrocyclobutabenzenes in the system I2-SbF5 . Russ J Org Chem 47, 1026–1034 (2011). https://doi.org/10.1134/S1070428011070104

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428011070104

Keywords

Search

Navigation