Skeletal reactions of perfluoromethylethyl- and perfluorodiethylbenzocyclobutenes with 1,1- and 1,2-alkyl groups in SbF5

Autor: G. G. Yakobson, Victor M. Karpov, V. E. Platonov, T. V. Mezhenkora
Rok vydání: 1990
Předmět:
Zdroj: Bulletin of the Academy of Sciences of the USSR Division of Chemical Science. 39:1000-1004
ISSN: 1573-9171
0568-5230
DOI: 10.1007/bf00961700
Popis: Taking perfluoro-1,1-dialkylbenzocyclobutenes as examples, it has been shown to be possible to enlarge the four-membered ring in polyfluorobenzocyclobutenes to five-membered in the presence of SbF5, by cleavage of the four-membered ring followed by cyclization of the resulting polyfluorostyrene to the polyfluoroindane, which then undergoes further reactions. Perfluoro-1-methyl-1-ethylbenzocyclobutene isomerizes at 50°C in the presence of SbF5 to perfluoro-α,β-o -trimethylstyrene, which is reversibly converted at 130°C into perfluoro-1,2-dimethylindane. Perfluoro-l,l-diethylbenzocyclobutene isomerizes at 130°C in the presence of SbF5 to give perfluoro-α -ethyl-β,o -dimethylstyrene, which at 170°C gives perfluoro-2-methyl-3-ethylindene- and perfluoro-2-methyl-3-ethyl-4,5,6,7-tetrahydroindene. The last two compounds, together with perfluoro-o-dipropylbenzene, are obtained from per fluoro-1,2-diethylbenzocyclobutene-with SbF5 at 170°C. From perfluoro-1-methyl-2-ethylbenzocyclobutene with SbF5 at 95°C there is obtained perfluoro-1-ethylindane, while at 130°C, in addition to the latter compound, there are obtained perfluorinated 1,1-dimethylindane, 1,2-dimethylindane, α,β,o-trimethylstyrene, 2,3-dimethylindene, and 2,3-dimethyl-4,5,6,7-tetrahydroindene.
Databáze: OpenAIRE
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