Advertisement

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

  • V. M. Karpov
  • T. V. Mezhenkova
  • V. E. Platonov
  • L. N. Shchegoleva
Organic Chemistry

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.

Keywords

Transition State Relative Energy Analogous Condition SbF5 Geometrical Optimization 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    V. M. Karpov, T. V. Mezhenkova, V. E. Platonov, and G. G. Yakobson, Bull. Soc. Chim. Fr., 980 (1986).Google Scholar
  2. 2.
    V. V. Bardin, G. G. Furin, and G. G. Yakobson, J. Fluorine Chem.,14, No. 6, 455 (1979).Google Scholar
  3. 3.
    Yu. V. Pozdnyakovich and V. D. Shteingarts, J. Fluorine Chem.,4, 283, 297 (1974).Google Scholar
  4. 4.
    M. J. S. Dewar and W. Thiel, J. Am. Chem. Soc.,99, No. 15, 4899, 4907 (1977).Google Scholar
  5. 5.
    A. A. Voityuk, Zh. Strukt. Khim.,29, No. 1, 138 (1988).Google Scholar
  6. 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. 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

Copyright information

© Plenum Publishing Corporation 1992

Authors and Affiliations

  • V. M. Karpov
    • 1
  • T. V. Mezhenkova
    • 1
  • V. E. Platonov
    • 1
  • L. N. Shchegoleva
    • 1
  1. 1.Novosibirsk Institute of Organic Chemistry, Siberian BranchAcademy of Sciences of the USSRUSSR

Personalised recommendations