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Isomerization of perfluoro-3,3-diethylindan-1-one into perfluoro-1,3-dimethyl-4-ethyl-1 H-isochromen under the action of antimony pentafluoride

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Abstract

The heating of perfluoro-3,3-diethylindan-1-one with SbF5 at 180°C after treatment of the reaction mixture with anhydrous HF afforded perfluoro-1,3-dimethyl-4-ethylisochromen, and after hydrolysis, perfluoro-1,3-dimethyl-4-ethyl-1H-isochromen-1-ol. The latter under the action of NaHCO3 converted into 5,6,7,8-tetrafluoro-1,3-bis(trifluoromethyl)-1H-isochromen-1-ol. Both isochromenols reacted with SOCl2 gave the corresponding polyfluoro-1-chloro-1H-isochromens. On dissolving isochromenols in CF3SO3H and isochromens in SbF5 perfluoro-1,3-dimethyl-4-ethylisochromenyl and 5,6,7,8-tetrafluoro-1,3-bis(trifluoromethyl)isochromenyl cations were generated which by hydrolysis were converted into the corresponding isochromenols.

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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

  2. Novosibirsk State University, Novosibirsk, Russia

    Ya. V. Zonov

Authors
  1. Ya. V. Zonov
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  2. V. M. Karpov
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  3. V. E. Platonov
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Correspondence to Ya. V. Zonov.

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Original Russian Text © Ya.V. Zonov, V.M. Karpova, V.E. Platonov, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 2, pp. 217–222.

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Zonov, Y.V., Karpov, V.M. & Platonov, V.E. Isomerization of perfluoro-3,3-diethylindan-1-one into perfluoro-1,3-dimethyl-4-ethyl-1 H-isochromen under the action of antimony pentafluoride. Russ J Org Chem 47, 207–213 (2011). https://doi.org/10.1134/S1070428011020096

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  • DOI: https://doi.org/10.1134/S1070428011020096

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