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Reaction of Polyfluorinated Benzocyclobutenes with Oleum

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Abstract

Perfluorinated 1-methyl- and 1-ethylbenzocyclobutenes and 2-methyl- and 2-ethylbenzocyclo­butenones reacted with 20% oleum at 150°C to give mixtures of almost equimolar amounts of 3-perfluoroalkyl-4,5,6,7-tetrafluorophthalides and perfluoro-3-hydroxy-3-alkylphthalides. In addition to these products, the reac­tion of perfluoro-2-methylbenzocyclobutenone with oleum at 100°C afforded perfluoro-2-hydroxy-2-methylbenzo­cyclobutenone. The reaction of perfluoro-2-phenylbenzocyclobutenone with oleum produced perfluoro-2-benzoylbenzoic acid, whereas polyfluorobenzocyclobutene-1,2-diols were converted to the corresponding cyclic sulfates.

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ACKNOWLEDGMENTS

The authors thank joint Chemical Research Center, Siberian Branch, Russian Academy of Sciences, for providing facilities for spectral and analytical studies.

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Authors and Affiliations

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

    D. S. Golokhvastova, Ya. V. Zonov, V. M. Karpov & T. V. Mezhenkova

  2. Novosibirsk State University, 630090, Novosibirsk, Russia

    D. S. Golokhvastova & Ya. V. Zonov

Authors
  1. D. S. Golokhvastova
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  2. Ya. V. Zonov
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  3. V. M. Karpov
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  4. T. V. Mezhenkova
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Correspondence to Ya. V. Zonov.

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Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 1, pp. 51–61 https://doi.org/10.31857/S0514749223010032.

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Golokhvastova, D.S., Zonov, Y.V., Karpov, V.M. et al. Reaction of Polyfluorinated Benzocyclobutenes with Oleum. Russ J Org Chem 59, 29–37 (2023). https://doi.org/10.1134/S1070428023010025

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  • DOI: https://doi.org/10.1134/S1070428023010025

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