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Reaction of perfluorobenzocycloalkenes with SiO2-SbF5 and skeleton transformations of their carbonyl derivatives in SbF5 medium

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Abstract

The reaction of perfluorinated benzocyclobutene and tetraline with SiO2-SbF5 led to the formation in a high yield of their mono- and further dicarbonyl derivatives. The monocarbonyl derivatives on heating with SbF5 underwent disproportionation into the corresponding perfluorobenzocycloalkenes and diketones. Both mono- and diketones in the SbF5 medium are liable to suffer skeleton rearrangements yielding five- and six-membered oxygen-containing heterocycles and/or products of the opening of the alicyclic fragment of the substrate, and from the perfluorobenzocyclobutenone compounds were also obtained with a number of carbon atoms greater than that of the initial ketone.

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Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, Novosibirsk, 630090, Russia

    Ya. V. Zonov, V. M. Karpov, V. E. Platonov & Yu. V. Gatilov

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  1. Ya. V. Zonov
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  2. V. M. Karpov
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  3. V. E. Platonov
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  4. Yu. V. Gatilov
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Corresponding author

Correspondence to V. M. Karpov.

Additional information

Original Russian Text © Ya.V. Zonov, V.M. Karpov, V.E. Platonov, Yu.V. Gatilov, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 2, pp. 212–226.

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Zonov, Y.V., Karpov, V.M., Platonov, V.E. et al. Reaction of perfluorobenzocycloalkenes with SiO2-SbF5 and skeleton transformations of their carbonyl derivatives in SbF5 medium. Russ J Org Chem 44, 202–217 (2008). https://doi.org/10.1134/S107042800802005X

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  • DOI: https://doi.org/10.1134/S107042800802005X

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