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V. R. Sinyakov - One of the best experts on this subject based on the ideXlab platform.
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Reaction of Perfluorobenzocyclobutene with Excess Pentafluorobenzene in SbF_5
Russian Journal of Organic Chemistry, 2018Co-Authors: T. V. Mezhenkova, V. M. Karpov, V. R. Sinyakov, Yu. V. Gatilov, Ya. V. Zonov, V. E. PlatonovAbstract:The reaction of perfluorobenzocyclobutene with excess pentafluorobenzene in SbF_5, followed by hydrolysis, gave a mixture of perfluoro-1,3,3-triphenyl-1,3-dihydro-2-benzofuran-1-ol, perfluoro-1,1,2-triphenylbenzocyclobuten- 5-one, and perfluoro-4-(2,2-diphenylbenzocyclobuten-1-ylidene)cyclohexa-2,5-dien-1- one. When the reaction mixture was treated for a long time with Olah’s reagent (HF–pyridine), isomeric perfluoro-9,10-diphenyl-1,4-, -1,10-, -2,9-, and -9,10-dihydroanthracenes were formed and were converted to perfluoro-9,10-diphenylanthracene by the action of SbF_5.
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Skeletal transformations of pentafluorophenylation products of perfluorinated 1,2-dialkyl-1,2-dihydrocyclobutabenzenes in SbF_5
Russian Journal of Organic Chemistry, 2013Co-Authors: T. V. Mezhenkova, V. M. Karpov, V. R. Sinyakov, V. E. PlatonovAbstract:Perfluorinated 1-ethyl-2-methyl- and 1-isopropyl-2-methyl-1,2-dihydrocyclobutabenzenes reacted with pentafluorobenzene in SbF_5 to generate perfluoro(1-ethyl-2-methyl-2-phenyl- and perfluoro(1-izopropyl-2-methyl-2-phenyl-1,2-dihydrocyclobutabenzen-1-yl) cations. These cations in SbF_5 at 20°C underwent opening of the four-membered ring and its expansion to five-membered. After hydrolysis, perfluorinated 4-[1-(2-propylphenyl)ethylidene]- and 4-[1-(2-isobutylphenyl)ethylidene]-2,5-cyclohexadien-1-ones were obtained together with perfluoro(3-ethyl- and perfluoro(3-isopropyl-2-phenylinden-1-ones).
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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
Russian Journal of Organic Chemistry, 2012Co-Authors: T. V. Mezhenkova, V. M. Karpov, V. R. Sinyakov, V. E. PlatonovAbstract: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-cyclohexadien-1-one} together with perfluoro[4b,10-diethylbenzo[ a ]azulen-7(4b H )-one] resulting from unusual expansion of the pentafluorobenzene ring to seven-membered ring. Analogous reaction at 90°C, apart from the above compounds, afforded perfluorinated 10-ethyl- and 3,10-diethylbenzo[ a ]azulen-6(10 H )-ones via elimination of C_2F_5 group from the seven-membered ring or its migration to the benzene ring.
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Expansion of the pentafluorobenzene ring of perfluoro-1,2-diethyl-1-phenylbenzocyclobutene under the action of SbF5
Journal of Fluorine Chemistry, 2008Co-Authors: Tatyana V. Mezhenkova, V. R. Sinyakov, Victor M. Karpov, Vyacheslav E. Platonov, Tatjana V. Rybalova, Yuri V. GatilovAbstract:Abstract Perfluoro-1,2-diethyl-1-phenylbenzocyclobutene under the action of SbF5 gives, after treatment of the reaction mixture with water, perfluoro-4-[1-(6-propyl-phenyl)-propylidene]cyclohexa-2,5-dienone along with the products of unusual pentafluorobenzene ring expansion – perfluorinated 4b,10-diethylbenzo[a]azulen-7(4bH)-one and 10-ethylbenzo[a]azulen-6(10H)-one.
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Reactions of perfluorinated 1-ethyltetrahydronaphthalene, 1-ethylindan, and 1,1-diethylindan with pentafluorobenzene in antimony pentafluoride
Russian Journal of Organic Chemistry, 2006Co-Authors: V. R. Sinyakov, V. M. Karpov, T. V. Mezhenkova, V. E. Platonov, T. V. Rybalova, Yu. V. GatilovAbstract:The reaction of perfluoro(1-ethyltetrahydronaphthalene) with pentafluorobenzene in SbF_5, followed by treatment of the reaction mixture with water, afforded a mixture of 1-hydroxyperfluoro(1-phenyl-4-ethyletetrahydronaphthalene) and perfluoro(5-phenyl-8-ethyl-2,6,7,8-tetrahydronaphthalen-2-one). From perfluoro(1,1-diethylindan), 1-hydroxyperfluoro(1,1-diethyl-3-phenylindan) was obtained. Perfluoro(1-ethylindan) reacted with an equimolar amount of pentafluorobenzene in SbF_5 to give (after hydrolysis) 1-hydroxyperfluoro-(3-ethyl-1-phenylindan), 1-hydroxyperfluoro(3-ethyl-1,3-diphenylindan), and perfluoro(1-ethyl-1-phenylindan), while in the reaction with excess pentafluorobenzene, followed by treatment with anhydrous hydrogen fluoride, perfluoro(1-ethyl-3-phenylindan) and perfluoro(1-ethyl-1,3-diphenylindan) were formed.
Xiangjun Shi - One of the best experts on this subject based on the ideXlab platform.
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Expedient Synthesis of Tetrafluorophenoxthiines and Derivatives by Copper(I)-Catalyzed Cross-Coupling Reaction.
ChemInform, 2014Co-Authors: Cuiling Zhang, Guanghui Yang, Xiangjun ShiAbstract:Pentafluorobenzene and aryl mercaptanes or the corresponding diaryl disulfides undergo an interesting oxidative coupling reaction to give tetrafluorophenoxthiines in moderate yields.
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Expedient synthesis of tetrafluorophenoxthiines and derivatives by copper(I)-catalyzed cross-coupling reaction
Journal of Fluorine Chemistry, 2013Co-Authors: Cuiling Zhang, Guanghui Yang, Xiangjun ShiAbstract:Abstract In this research, tetrafluorophenoxthiines were successfully synthesized from pentafluorobenzene and aryl thiols or diaryl disulfides in the presence of copper catalyst and ligand by using O 2 as the oxidant, t -BuOLi as the base at 100 °C. The ligand ( E )-3-(dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one ( L ) played an indispensable role in the reaction. This work contains a notable mode of C F bond activation, which is in the ortho position to the C H bond of pentafluorobenzene.
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Copper‐Catalyzed Direct Thiolation of Pentafluorobenzene with Diaryl Disulfides or Aryl Thiols by C–H and C–F Bond Activation
European Journal of Organic Chemistry, 2012Co-Authors: Cuiling Zhang, Xiangjun ShiAbstract:A Cu-catalyzed cross-coupling reaction of diaryl disulfides or aryl thiols with pentafluorobenzene using CuBr as the catalyst, tBuOLi or tBuOK as the base in DMSO at 60 °C under an O2 atmosphere was investigated. The corresponding bisarylthiolation products were obtained in moderate to good yields by C–H bond and C–F bond activation. When 1,10-phenanthroline·H2O and DDQ were added to the above system, monoarylthiolation products, with/without bisarylthiolation products, could be isolated in moderate yields. A plausible mechanism for these transformations was given. Thus, it represents a method for the synthesis of polyfluorinated diaryl sulfides and polyfluorinated triarylbisulfides throughC–H bond and C–F bond activation.
Bin Zhang - One of the best experts on this subject based on the ideXlab platform.
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Selective C4—F Bond Cleavage of Pentafluorobenzene: Synthesis of N-Tetrafluoroarylated Heterocyclic Compounds.
ChemInform, 2013Co-Authors: Cuibo Liu, Huan Wang, Xing Xing, Bin ZhangAbstract:Aromatic nucleophilic substitution of Pentafluorobenzenes with a variety of N-heterocycles offers a convenient synthesis of N-tetrafluoroarylated derivatives.
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Selective C4–F bond cleavage of pentafluorobenzene: synthesis of N-tetrafluoroarylated heterocyclic compounds
Tetrahedron Letters, 2013Co-Authors: Cuibo Liu, Huan Wang, Xing Xing, Bin ZhangAbstract:A simple aromatic nucleophilic monosubstitution reaction for the synthesis of N-tetrafluoroarylated heterocyclic compounds via selective C4–F bond cleavage of pentafluorobenzene with N–H containing heterocycles is demonstrated. This method is highly tolerant of a wide range of substrates to give the corresponding products in moderate to good yields. Additionally, this strategy is applied to synthesize other mono-, di-, and tri-fluoroarylated indole derivatives.
V. E. Platonov - One of the best experts on this subject based on the ideXlab platform.
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Reaction of Perfluorobenzocyclobutene with Excess Pentafluorobenzene in SbF_5
Russian Journal of Organic Chemistry, 2018Co-Authors: T. V. Mezhenkova, V. M. Karpov, V. R. Sinyakov, Yu. V. Gatilov, Ya. V. Zonov, V. E. PlatonovAbstract:The reaction of perfluorobenzocyclobutene with excess pentafluorobenzene in SbF_5, followed by hydrolysis, gave a mixture of perfluoro-1,3,3-triphenyl-1,3-dihydro-2-benzofuran-1-ol, perfluoro-1,1,2-triphenylbenzocyclobuten- 5-one, and perfluoro-4-(2,2-diphenylbenzocyclobuten-1-ylidene)cyclohexa-2,5-dien-1- one. When the reaction mixture was treated for a long time with Olah’s reagent (HF–pyridine), isomeric perfluoro-9,10-diphenyl-1,4-, -1,10-, -2,9-, and -9,10-dihydroanthracenes were formed and were converted to perfluoro-9,10-diphenylanthracene by the action of SbF_5.
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Reaction of difluoromethyl pentafluorophenyl sulfoxide with nucleophiles
Russian Journal of Organic Chemistry, 2017Co-Authors: B. V. Koshcheev, V. E. Platonov, A. M. Maksimov, V. V. ShelkovnikovAbstract:Reactions of 1-(difluoromethanesulfinyl)pentafluorobenzene with sodium methoxide, sodium phenoxide, potassium hydrosulfide, and methylamine resulted in substitution of fluorine atom in the 4-position (in the reaction with methylamine, also in the 2-position). Treatment of the title compound with sodium hydroxide afforded pentafluorobenzene due to cleavage of the C_arom‒S bond.
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Skeletal transformations of pentafluorophenylation products of perfluorinated 1,2-dialkyl-1,2-dihydrocyclobutabenzenes in SbF_5
Russian Journal of Organic Chemistry, 2013Co-Authors: T. V. Mezhenkova, V. M. Karpov, V. R. Sinyakov, V. E. PlatonovAbstract:Perfluorinated 1-ethyl-2-methyl- and 1-isopropyl-2-methyl-1,2-dihydrocyclobutabenzenes reacted with pentafluorobenzene in SbF_5 to generate perfluoro(1-ethyl-2-methyl-2-phenyl- and perfluoro(1-izopropyl-2-methyl-2-phenyl-1,2-dihydrocyclobutabenzen-1-yl) cations. These cations in SbF_5 at 20°C underwent opening of the four-membered ring and its expansion to five-membered. After hydrolysis, perfluorinated 4-[1-(2-propylphenyl)ethylidene]- and 4-[1-(2-isobutylphenyl)ethylidene]-2,5-cyclohexadien-1-ones were obtained together with perfluoro(3-ethyl- and perfluoro(3-isopropyl-2-phenylinden-1-ones).
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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
Russian Journal of Organic Chemistry, 2012Co-Authors: T. V. Mezhenkova, V. M. Karpov, V. R. Sinyakov, V. E. PlatonovAbstract: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-cyclohexadien-1-one} together with perfluoro[4b,10-diethylbenzo[ a ]azulen-7(4b H )-one] resulting from unusual expansion of the pentafluorobenzene ring to seven-membered ring. Analogous reaction at 90°C, apart from the above compounds, afforded perfluorinated 10-ethyl- and 3,10-diethylbenzo[ a ]azulen-6(10 H )-ones via elimination of C_2F_5 group from the seven-membered ring or its migration to the benzene ring.
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Reactions of perfluorinated 1-ethyltetrahydronaphthalene, 1-ethylindan, and 1,1-diethylindan with pentafluorobenzene in antimony pentafluoride
Russian Journal of Organic Chemistry, 2006Co-Authors: V. R. Sinyakov, V. M. Karpov, T. V. Mezhenkova, V. E. Platonov, T. V. Rybalova, Yu. V. GatilovAbstract:The reaction of perfluoro(1-ethyltetrahydronaphthalene) with pentafluorobenzene in SbF_5, followed by treatment of the reaction mixture with water, afforded a mixture of 1-hydroxyperfluoro(1-phenyl-4-ethyletetrahydronaphthalene) and perfluoro(5-phenyl-8-ethyl-2,6,7,8-tetrahydronaphthalen-2-one). From perfluoro(1,1-diethylindan), 1-hydroxyperfluoro(1,1-diethyl-3-phenylindan) was obtained. Perfluoro(1-ethylindan) reacted with an equimolar amount of pentafluorobenzene in SbF_5 to give (after hydrolysis) 1-hydroxyperfluoro-(3-ethyl-1-phenylindan), 1-hydroxyperfluoro(3-ethyl-1,3-diphenylindan), and perfluoro(1-ethyl-1-phenylindan), while in the reaction with excess pentafluorobenzene, followed by treatment with anhydrous hydrogen fluoride, perfluoro(1-ethyl-3-phenylindan) and perfluoro(1-ethyl-1,3-diphenylindan) were formed.
Yuri V. Gatilov - One of the best experts on this subject based on the ideXlab platform.
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Expansion of the pentafluorobenzene ring of perfluoro-1,2-diethyl-1-phenylbenzocyclobutene under the action of SbF5
Journal of Fluorine Chemistry, 2008Co-Authors: Tatyana V. Mezhenkova, V. R. Sinyakov, Victor M. Karpov, Vyacheslav E. Platonov, Tatjana V. Rybalova, Yuri V. GatilovAbstract:Abstract Perfluoro-1,2-diethyl-1-phenylbenzocyclobutene under the action of SbF5 gives, after treatment of the reaction mixture with water, perfluoro-4-[1-(6-propyl-phenyl)-propylidene]cyclohexa-2,5-dienone along with the products of unusual pentafluorobenzene ring expansion – perfluorinated 4b,10-diethylbenzo[a]azulen-7(4bH)-one and 10-ethylbenzo[a]azulen-6(10H)-one.