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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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