Abstract: In the presence of antimony pentafluoride at 130 degreesC, the four-membered ring of perfluoro-1-(2-ethylphenyl)benzocyclobutene (2) undergoes cleavage, forming perfluoro-2-ethyl-2'-methyldiphenylmethane (5). Compound 5 is converted, under the action of SbF5 at 170 degreesC, to perfluoro-8,9-dimethyl-1,2,3,4-tetrahydrofluorene (8). Perfluoro-1-(4-ethylphenyl)benzocyclobutene (3) remains unchanged at 130 C, whereas at 170 C it gives a mixture of perfluorinated 4'-ethyl-2-methyldiphenylmethane (9), 6-ethyl-1,2,3,4-tetrahydroanthracene (11) and 2-ethyl-9, 10-dihydroanthracene (12). When heated with SbF5 at 170 degreesC, perfluoro-1-phenylbenzocyclobutene (1) remains unchanged. Solution of compounds 2, 3, 5 and 9 in SbF5-SO2CIF generated the perfluorinated 1-(2-ethylphenyl)-1-benzocyclobutenyl (29), 1-(4-ethylphenyl)-1-benzocyclobutenyl (30), 2-ethyl-2'-methyldiphenylmethyl (31) and 4'-ethyl-2-methyldiphenylmethyl (32) cations, respectively. (C) 2002 Elsevier Science B.V. All rights reserved.

Cite: Karpov V. , Mezhenkova T. , Platonov V. , Sinyakov V.
Cationoid rearrangements in reactions of perflupro-1-arylbenzocyclobutenes with antimony pentafluoride
Journal of Fluorine Chemistry. 2002. V.117. N1. PII S0022-1139(02)00196-3 . DOI: 10.1016/S0022-1139(02)00196-3 WOS Scopus РИНЦ

Dates:

Published print:

Sep 1, 2002

Identifiers:

Web of science	WOS:000178527000013
Scopus	2-s2.0-0037190259
Elibrary	13404133
OpenAlex	W2951865213

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