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://stomuniver.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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Меженкова Т.В., Комаров В.В., Карпов В.М., Синяков В.Р., Зонов Я.В., Краснов В.И. ЖОрХ. 2021, 57, 1132–1145. [Mezhenkova T.V., Komarov V.V., Karpov V.M., Sinyakov V.R., Zonov Ya.V., Krasnov V.I. Russ. J. Org. Chem. 2021, 57, 1256–1267]. doi: 10.1134/S1070428021080042
Меженкова Т.В., Синяков В.Р., Карпов В.М., Зонов Я.В., Гатилов Ю.В., Платонов В.Е. ЖОрХ. 2018, 54, 546–553. [Mezhenkova T.V., Sinyakov V.R., Karpov V.M., Zonov Ya.V., Gatilov Yu.V., Platonov V.E. Russ. J. Org. Chem. 2018, 54, 545–553]. doi: 10.1134/S107042801804005X
Карпов В.М., Меженкова Т.В., Платонов В.Е., Синяков В.Р., Щеголева Л.Н. ЖОрХ. 2002, 38, 1210–1217. [Karpov V.M., Mezhenkova T.V., Platonov V.E., Sinyakov V.R., Shchegoleva L.N. Russ. J. Org. Chem. 2002, 38, 1158–1165]. doi: 10.1023/A:1020901526459
Pozdnyakovich Yu.V., Shteingarts V.D. J. Fluor. Chem. 1974, 4, 283–296. doi: 10.1016/S0022-1139(00)80865-9
Pozdnyakovich Yu.V., Shteingarts V.D. J. Fluor. Chem. 1974, 4, 297–316. doi: 10.1016/S0022-1139(00)80866-0
Платонов В.Е., Сенченко Т.В., Якобсон Г.Г. ЖОрХ. 1976, 12, 816–821. [Platonov V.E, Senchenko T.V., Yakobson G.G. Russ. J. Org. Chem. 1976, 12, 818–823.