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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Authors: | Ya V Zonov V M Karpov V E Platonov |
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Institution: | 1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, Novosibirsk, 630090, Russia 2. Novosibirsk State University, Novosibirsk, Russia
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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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