Formation of 1-(2,4,6-trifluorophenyl)perfluorobenzocyclobutene from perfluorobenzocyclobutene and 1,3,5-trifluorobenzene and its interaction with polyfluorobenzenes in an SbF 5  medium

T. V. Mezhenkova; Меженкова Т. В.; V. V. Komarov; Комаров В. В.; V. M. Karpov; Карпов В. М.; Ya. V. Zonov; Зонов Я. В.; V. I. Krasnov; Краснов В. И.

doi:10.31857/S0514749225030028

Formation of 1-(2,4,6-trifluorophenyl)perfluorobenzocyclobutene from perfluorobenzocyclobutene and 1,3,5-trifluorobenzene and its interaction with polyfluorobenzenes in an SbF₅ medium

Authors: Mezhenkova T.V.¹, Komarov V.V.¹, Karpov V.M.¹, Zonov Y.V.¹, Krasnov V.I.¹
Affiliations:
1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences
Issue: Vol 61, No 3 (2025)
Pages: 230-239
Section: ЭКСПЕРИМЕНТАЛЬНЫЕ СТАТЬИ
URL: https://pediatria.orscience.ru/0514-7492/article/view/687763
DOI: https://doi.org/10.31857/S0514749225030028
EDN: https://elibrary.ru/ETCEKA
ID: 687763

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Abstract

Interaction of perfluorobenzocyclobutene with two equivalents of 1,3,5-trifluorobenzene in an SbF₅ medium followed by the treatment of the reaction mixture with water gave (3,4,5,6-tetrafluorobenzene-1,2-diyl)bis[(2,4,6-trifluorophenyl)methanone], 1-(2,4,6-trifluorophenyl)perfluorobenzocyclobuten-1-ol and 4,5,6,7-tetrafluoro-1,3,3-tris(2,4,6-trifluorophenyl)-1,3-dihydro-2-benzofuran-1-ol. When the reaction mixture was treated with HF, 1,2-bis(2,4,6-trifluorophenyl)-perfluorobenzocyclobutene along with 1-(2,4,6-trifluorophenyl)perfluorobenzocyclobutene were obtained. The latter compound reacted with pentafluoro-, 1,2,3,4- or 1,2,4,5-tetrafluorobenzenes in an SbF₅ medium to give corresponding polyfluoro-1,2-diphenylbenzocyclobutenes after treatment of the reaction mixture with HF.

Keywords

perfluorobenzocyclobutene, trifluorobenzene, tetrafluorobenzene, pentafluorobenzene, cation, skeletal transformations, antimony pentafluoride

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