Transformations of perfluorinated 1-alkyl-, 1-phenyl- and 1,2-dialkylbenzocyclobutenes under the action of SiO2/SbF5

Transformations of perfluorinated 1-alkyl-, 1-phenyl- and 1,2-dialkylbenzocyclobutenes under the action of SiO2/SbF5 Full article

Journal

Journal of Fluorine Chemistry
ISSN: 0022-1139

Output data

Year: 2013, Volume: 145, Pages: 41-50 Pages count : DOI: 10.1016/j.jfluchem.2012.11.004

Tags

Perfluorinated; Benzocyclobutenes; Phthalides; Phthalanes; Silicon dioxide; Antimony pentafluoride

Authors

Zonov Yaroslav V. ¹ , Karpov Victor M. ¹ , Platonov Vyacheslav E. ¹ , Rybalova Tatjana V. ¹

Affiliations

1	(Данные Web of science) NN Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia

Heating of perfluorinated 1-methyl-, 1-ethyl- and 1-isopropylbenzocyclobutenes with SiO2 in an SbF5 medium at 75 degrees C results in perfluoro-2-alkylbenzocyclobutenones or perfluoro-3-alkylphthalides formation. Perfluorinated 1,2-diethyl- and 1-ethyl-2-methylbenzocyclobutenes react with SiO2/SbF5 at 75 degrees C to form, after treatment of the reaction mixture with water, perfluorinated 1,3-diethyl- and 1-ethyl-3-methylphthalan-1,3-diol, respectively. Perfluoro-1,2-diisopropylbenzocyclobutene under the action of SiO2/SbF5 at 95 degrees C is converted to perfluoro-7,8-diisopropylbicyclo[4.2.0]octa-1,5,7-triene-3,4-dione and perfluoro-1,2-diisobutyrylbenzene. Perfluoro-1-methyl-2-phenylbenzocyclobutene does not react with SiO2 in an SbF5 medium at 75 degrees C, perfluoro-1-phenylbenzocyclobutene in analogous conditions gives a mixture of perfluorinated 2-hydroxy-2-phenylbenzocyclobutenone and 2-benzoylbenzoic acid. (c) 2012 Elsevier B.V. All rights reserved.

Zonov Y.V. , Karpov V.M. , Platonov V.E. , Rybalova T.V.
Transformations of perfluorinated 1-alkyl-, 1-phenyl- and 1,2-dialkylbenzocyclobutenes under the action of SiO2/SbF5
Journal of Fluorine Chemistry. 2013. V.145. P.41-50. DOI: 10.1016/j.jfluchem.2012.11.004 WOS Scopus РИНЦ

Published print:

Jan 1, 2013

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