The alicyclic ring cleavage and other transformations of perfluorinated 1-alkyl-, 1,1- and 1,2-dialkyl-benzocyclobutenes in the system Br-2-SbF5

The alicyclic ring cleavage and other transformations of perfluorinated 1-alkyl-, 1,1- and 1,2-dialkyl-benzocyclobutenes in the system Br-2-SbF5 Full article

Journal

Journal of Fluorine Chemistry
ISSN: 0022-1139

Output data

Year: 1996, Volume: 77, Number: 2, Pages: 133-137 Pages count : 5 DOI: 10.1016/0022-1139(96)03390-8

Tags

alicyclic ring cleavage; perfluoroalkyl benzocyclobutenes; perfluorodialkylbenzocyclobutenes; Br3SbF5 system; NMR spectroscopy; mass spectrometry

Authors

Karpov V.M. ¹ , Mezhenkova T.V. ¹ , Platonov V.E. ¹

Affiliations

1	Institute of Organic Chemistry, Novosibirsk 630090, Russian Federation

In the reactions of perfluorinated 1-methyl- (2) and 1-ethyl-benzocyclobutene (3) with bromine in an SbF5 medium, cleavage of the four-membered ring of the starting compounds giving 2-bromoperfluoroisopropylbenzene (8) and 2-bromoperfluoro-sec-butylbenzene (9), respectively, was observed. In the system Br-2-SbF5, perfluorinated 1,1- (4) and 1,2-diethylbenzocyclobutene (5) undergo bromofluorination of the aromatic ring and breaking of the C-1-C-2 bond of the four-membered ring. Thus, in the Br-2-SbF5, system, compound 5 gives 4-bromoperfluoro-1,2-dipropylcyclohexene (10) and perfluoro-1,2-dipropylcyclohexene (11), and isomer 4 gives perfluoro-1,1-diethyl-3,4,5,6-tetrahydrobenzocyclobutene (15) and perfluoro-1-methyl-2-(pent-2-ene-3-yl)cyclohexene (16). The latter is obtained by heating compound 15 with SbF5 or CsF.

Karpov V.M. , Mezhenkova T.V. , Platonov V.E.
The alicyclic ring cleavage and other transformations of perfluorinated 1-alkyl-, 1,1- and 1,2-dialkyl-benzocyclobutenes in the system Br-2-SbF5
Journal of Fluorine Chemistry. 1996. V.77. N2. P.133-137. DOI: 10.1016/0022-1139(96)03390-8 WOS Scopus РИНЦ

Published print:

Apr 1, 1996

Web of science	WOS:A1996UV33300005
Scopus	2-s2.0-0030120196
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