Abstract: 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-degrees-C in the presence of SbF5 to perfluoro-alpha,beta-omicron-trimethylstyrene, which is reversibly converted at 130-degrees-C into perfluoro-1,2-dimethylindane. Perfluoro-1,1-diethylbenzocyclobutene isomerizes at 130-degrees-C in the presence of SbF5 to give perfluoro-alpha-ethyl-beta,o-dimethylstyrene, which at 170-degrees-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 perfluoro-1,2-diethylbenzocyclobutene with SbF5 at 170-degrees-C. From perfluoro-1-methyl-2-ethyl-benzocyclobutene with SbF5 at 95-degrees-C there is obtained perfluoro-1-ethylindane, while at 130-degrees-C, in addition to the latter compound, there are obtained perfluorinated 1,1-dimethylindane, 1,2-dimethylindane, alpha,beta,o-trimethylstyrene, 2,3-dimethylindene, and 2,3-dimethyl-4,5,6,7-tetrahydroindene.

Cite: Karpov V.M. , Mezhenkova T.V. , Platonov V.E. , Yakobson G.G.
SKELETAL REACTIONS OF PERFLUOROMETHYLETHYLBENZOCYCLOBUTANES AND PERFLUORODIETHYLBENZOCYCLOBUTENES WITH 1,1-ALKYL AND 1,2-ALKYL GROUPS IN SBF5
Bulletin of the Academy of Sciences of the USSR Division of Chemical Science. 1990. V.39. N5. P.1000-1004. DOI: 10.1007/BF00961700 WOS Scopus РИНЦ

Dates:

Published print:

May 1, 1990

Identifiers:

Web of science	WOS:A1990EX32300009
Scopus	2-s2.0-34249928930
Elibrary	30832144
OpenAlex	W2055784265

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