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Article
Synthesis of 1-(2,4,6-Trifluorophenyl)perfluorobenzocyclobutene from Perfluorobenzocyclobutene and 1,3,5-Trifluorobenzene and Its Reaction with Polyfluorobenzenes in an SbF5 Medium
The reaction 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)bi...
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Article
Carbonylation and Other Transformations of Polyfluorobenzocyclobutenols in Superacids
Acid-catalyzed carbonylation of a series of polyfluorinated benzocyclobuten-1-ols, as well as cyclic sulfuric acid esters derived from benzocyclobutene-1,2-diols, with carbon monoxide in the presence of TfOH a...
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Article
Reaction of Polyfluorinated Benzocyclobutenes with Oleum
Perfluorinated 1-methyl- and 1-ethylbenzocyclobutenes and 2-methyl- and 2-ethylbenzocyclobutenones reacted with 20% oleum at 150°C to give mixtures of almost equimolar amounts of 3-perfluoroalkyl-4,5,6,7-tetr...
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Article
Biradical with a polyfluorinated terphenylene backbone
A method was developed for the synthesis of perfluoro-1,1′:4′,1″-terphenyl by the reaction of chloroperfluorobenzene with zinc dust followed by the reaction of the resulting mixture of C6F5ZnCl and (C6F5)2Zn with...
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Article
Reduction of Perfluorinated Benzocycloalkenones and Other Polyfluoroaryl Ketones to Alcohols with LiBH4
The reduction of polyfluorinated benzocycloalken-1-ones, perfluoro-2,3-dihydrobenzofuran-3-one, and perfluorinated diaryl and alkyl aryl ketones with lithium tetrahydridoborate in diethyl ether gave the corre...
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Article
Reaction of Perfluorobenzocyclobutene with Isomeric Tetrafluorobenzenes in an SbF5 Medium
The reaction of perfluorobenzocyclobutene (1 mol) with isomeric tetrafluorobenzenes (2 mol) in an SbF5 medium resulted in the isolation of 1,2-bis(tetrafluorophenyl)perfluorocyclobutene after treatment of the rea...
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Article
An efficient approach to the synthesis of 2,3,4,5-tetrafluorophenol
A new method for the preparation of 2,3,4,5-tetrafluorophenol from 2-[(2,3,4,5,6-pentafluorophenyl)thio]acetic acid has been proposed. It included the intramolecular cyclization of the salt of this acid in the...
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Article
Skeletal Transformations of the Arylation Products of Perfluoro(1,2-diethylbenzocyclobutene) with Tetrafluorobenzenes in the Presence of SbF5
The reaction of perfluoro(1,2-diethylbenzocyclobutene) with 1,2,4,5-tetrafluorobenzene in SbF5, followed by hydrolysis, gave products resulting from expansion of the tetrafluorophenyl ring to cycloheptatriene. Th...
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Article
Carbonylation of Polyfluorobenzocyclobutenones in a SbF5 Medium
The carbonylation of perfluoro-2-R-benzocyclobutenones (R = F, CF3, C2F5, C6F5) in a CO-SbF5 system is accompanied by transformations of the four-membered cycle in the substrate to form polyfluorinated 1H-isochro...
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Article
Generation of Perfluoro- and 1-Chloroperfluoro-Indanyl and -Benzocyclobutenyl Cations with Perfluoroalkyl Groups in the Aliphatic Ring
Perfluoro(alkylbenzocycloalken-1-yl) cations were generated in a SbF5−SO2ClF medium from perfluorinated indane and benzocyclobutene derivatives containing perfluoroalkyl groups in the alicyclic fragment. The cati...
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Article
Reaction of Perfluorobenzocyclobutene with Excess Pentafluorobenzene in SbF5
The reaction of perfluorobenzocyclobutene with excess pentafluorobenzene in SbF5, followed by hydrolysis, gave a mixture of perfluoro-1,3,3-triphenyl-1,3-dihydro-2-benzofuran-1-ol, perfluoro-1,1,2-triphenylbenzoc...
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Article
X-Ray Diffraction Study of Perfluoro- 9,10-Diphenylanthracene and Perfluoro- 9,10-Diphenyldihydroanthracenes
The molecular and crystal structure of perfluoro-9,10-diphenylanthracene and its perfluorinated dihydro derivatives (9,10-diphenyl-1,4-dihydroanthracene, 9,10-diphenyl-2,9-dihydroanthracene, and cis,trans- 9,10-d...
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Article
Synthesis of (6,7-dichlorononafluoro-5,6,7,8-tetrahydronaphthalen-2-yl)acetic acid and its transformation into perfluorinated 2-methylnaphthalene and 6-methyl-1,4-dihydronaphthalene
2,3-Dichlorodecafluorotetralin reacted with ethyl cyanoacetate to give ethyl 2-cyano-2-(6,7-dichlorononafluoro-5,6,7,8-tetrahydronaphthalen-2-yl)acetate which was hydrolyzed to (6,7-dichlorononafluoro-5,6,7,8-...
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Article
Chlorination and decarboxylation of (heptafluoronaphthalen-2-yl)acetic acid. Synthesis of 2-(dichloromethyl)- and 2-(difluoromethyl)heptafluoronaphthalenes
Decarboxylation of (heptafluoronaphthalen-2-yl)acetic acid in DMF in the presence of NaHCO3 gave 2-methylheptafluoronaphthalene, and treatment with PCl5 on heating afforded dichloro(heptafluoronaphthalen-2-yl)ace...
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Article
Skeletal transformations of pentafluorophenylation products of perfluorinated 1,2-dialkyl-1,2-dihydrocyclobutabenzenes in SbF5
Perfluorinated 1-ethyl-2-methyl- and 1-isopropyl-2-methyl-1,2-dihydrocyclobutabenzenes reacted with pentafluorobenzene in SbF5 to generate perfluoro(1-ethyl-2-methyl-2-phenyl- and perfluoro(1-izopropyl-2-methyl-2...
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Article
Generation of perfluoro- and 1-chloropolyfluorobenzocycloalken-1-yl cations and their relative stability
Treatment of perfluorinated benzocyclobutene, indan, and tetralin with SbF5-SO2Cl2, as well as of their 1,1-dichloro analogs with SbF5, gave 1-chloropolyfluorobenzocycloalken-1-yl cations whose structure was stud...
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Article
Expansion of the pentafluorobenzene ring and other skeletal transformations in the reaction of perfluoro(1,2-diethyl-1-phenyl-1,2-dihydrocyclobutabenzene) with antimony pentafluoride
The reaction of perfluoro(1-phenyl-1,2-diethyl-1,2-dihydrocuclobutabenzene) with SbF5 at 20°C, followed by treatment of the reaction mixture with water gave perfluoro {4-[1-(2-propylphenyl)propylidene]-2,5-cyc...
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Article
Opening of the four-membered ring in perfluorinated 1-alkyl-2-phenyl- and 1-aryl-1,2-dihydrocyclobutabenzenes in the system I2-SbF5
Reactions of perfluorinated 1-phenyl-, 1-(2-ethylphenyl)-, 1-(4-ethylphenyl)-, 1-methyl-2-phenyl-, and 1-ethyl-2-phenyl-1,2-dihydrocyclobutabenzenes with iodine in antimony pentafluoride at 130°C, followed by ...
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Article
Formation of fluorene and anthracene derivatives in reactions of perfluorinated 1-alkyl-1-phenyl- and 1-alkyl-2-phenyl-1,2-dihydrocylobutabenzenes with antimony pentafluoride
The reaction of perfluoro(1-methyl-1-phenyl-1,2-dihydrocyclobutabenzene) with SbF5 at 50°C, followed by hydrolysis, gave perfluoro(1-phenylindan-1-ol), while analogous reaction at 90°C afforded perfluoro[10-methy...
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Article
Formation of perfluorinated 1,2-dialkylbenzenes from perfluoroalkylbenzocyclobutenes in the system I2-SbF5
