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Thermolytic transformations of polyfluoroorganic compounds

30. Copyrolysis of α,α-dichlorooctafluoroethylbenzene with tetrafluoroethylene

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Abstract

The reaction of α,α-dichlorooctafluoroethylbenzene with tetrafluoroethylene as a source of difluorocarbene has been studied. The copyrolysis of these compounds gave not only the expected products, decafluoro-α-methylstyrene and α-chloroheptafluorostyrene, but also noticeable amounts of perfluoro-1-methylindan and perfluoro-7-methylbicyclo[4.3.0]nona-1,4,6-triene along with perfluoro-3-methylindene and octafluorostyrene. It has been suggested that indan and the triene are formed with the participation of the C6F5CCICF3 radical through sigmatropic shifts of fluorine atoms in the intermediate bicyclic compounds. The reaction of α,α-dichlorodecafluoropropylbenzene with tetrafluoroethylene afforded α-chloroheptafluorostyrene as the main product.

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Authors and Affiliations

  1. Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent'eva, 630090, Novosibirsk, Russian Federation

    K. V. Dvornikova, V. E. Platonov & G. G. Yakobson

Authors
  1. K. V. Dvornikova
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  2. V. E. Platonov
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  3. G. G. Yakobson
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Additional information

For part 29, see Ref. 1.

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1767–1770, October, 1993.

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Dvornikova, K.V., Platonov, V.E. & Yakobson, G.G. Thermolytic transformations of polyfluoroorganic compounds. Russ Chem Bull 42, 1690–1693 (1993). https://doi.org/10.1007/BF00697041

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