Skip to main content
SpringerLink
Log in

Formation of o-H-perfluoroalkylbenzenes from polyfluorobenzocyclobutenes in the HF-SbF5 system

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Abstract

HF adds to perfluorinated benzocyclobutene, 1-methyl-, and 1-ethylbenzocyclobutenes in the presence of SbF5 to give o-H-perfluoroethyl, o-H-perfluoroisopropyl-, and o-H-perfluoro-sec-butylbenzenes, respectively. The ease of this reaction decreases in the same order. Perfluoro-1,1- and perfluoro-1,2-diethylbenzocyclobutenes, perfluoroindane, and perfluorotetralin are virtually unaltered under analogous conditions. The difference in the behavior of benzocyclobutenes may be related to the stability of the carbocations, which are intermediates or models of the transition state. This is in accord with the results of MNDO calculations with complete geometrical optimization for the relative energies of the starting compounds and intermediate ions.

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

Literature cited

  1. V. M. Karpov, T. V. Mezhenkova, V. E. Platonov, and G. G. Yakobson, Bull. Soc. Chim. Fr., 980 (1986).

  2. V. V. Bardin, G. G. Furin, and G. G. Yakobson, J. Fluorine Chem.,14, No. 6, 455 (1979).

    Google Scholar 

  3. Yu. V. Pozdnyakovich and V. D. Shteingarts, J. Fluorine Chem.,4, 283, 297 (1974).

    Google Scholar 

  4. M. J. S. Dewar and W. Thiel, J. Am. Chem. Soc.,99, No. 15, 4899, 4907 (1977).

    Google Scholar 

  5. A. A. Voityuk, Zh. Strukt. Khim.,29, No. 1, 138 (1988).

    Google Scholar 

  6. L. M. Yagupol'skii, Aromatic and Heterocyclic Compounds with Fluorine-Containing Sub-stituents [in Russian], Naukova Dumka, Kiev (1968), p. 229.

    Google Scholar 

  7. J. Emsley, J. Finney, and L. Sutcliffe, High-Resolution Nuclear Magnetic Resonance Spectroscopy [Russian translation], Vol. 2, Mir, Moscow (1969), p. 215.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Novosibirsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR, USSR

    V. M. Karpov, T. V. Mezhenkova, V. E. Platonov & L. N. Shchegoleva

Authors
  1. V. M. Karpov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. T. V. Mezhenkova
    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

  4. L. N. Shchegoleva
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2618–2622, November, 1991.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Karpov, V.M., Mezhenkova, T.V., Platonov, V.E. et al. Formation of o-H-perfluoroalkylbenzenes from polyfluorobenzocyclobutenes in the HF-SbF5 system. Russ Chem Bull 40, 2292–2296 (1991). https://doi.org/10.1007/BF00961054

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00961054

Keywords

Search

Navigation