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Keywords = antimony pentafluoride

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33 pages, 3420 KiB  
Article
Carbonylation of Polyfluorinated Alkylbenzenes and Benzocycloalkenes at the Benzyl C-F and C-Cl Bonds Under the Action of CO/SbF5
by Yaroslav V. Zonov, Siqi Wang, Vladislav V. Komarov, Victor M. Karpov, Dmitriy A. Parkhomenko and Tatyana V. Mezhenkova
Molecules 2025, 30(4), 931; https://doi.org/10.3390/molecules30040931 - 17 Feb 2025
Viewed by 905
Abstract
The carbonylation at the benzyl C-Hal bonds (Hal = F, Cl) of a number of polyfluorinated alkylbenzenes and benzocycloalkenes using carbon monoxide in the presence of SbF5 is described. The reaction provided the corresponding α-arylcarboxylic acids or their methyl esters following [...] Read more.
The carbonylation at the benzyl C-Hal bonds (Hal = F, Cl) of a number of polyfluorinated alkylbenzenes and benzocycloalkenes using carbon monoxide in the presence of SbF5 is described. The reaction provided the corresponding α-arylcarboxylic acids or their methyl esters following aqueous or methanol treatment. The products of double carbonylation were obtained from bis(chloromethyl)tetrafluorobenzenes and benzal fluorides. For benzal chloride derivatives, the possibility of selective mono- or dicarbonylation was shown to depend on the amount of antimony pentafluoride. In the case of polyfluorinated secondary benzyl halides with a hydrogen atom at the α-carbon atom and vicinal fluorine atoms, the addition of CO was found to be accompanied by the elimination of HF, resulting in α,β-unsaturated α-arylcarboxylic acids. The double elimination of HF during the carbonylation of 1,4-dichloro-2,2,3,3,5,6,7,8-octafluorotetralin yielded dimethyl perfluoronaphthalene-1,4-dicarboxylate. Full article
(This article belongs to the Section Organic Chemistry)
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6 pages, 1817 KiB  
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Perfluoro-3-ethyl-1,2,3,10b-tetrahydrofluoranthene
by Vladislav V. Komarov, Vyacheslav I. Krasnov, Victor M. Karpov, Dmitriy A. Parkhomenko and Tatyana V. Mezhenkova
Molbank 2024, 2024(3), M1842; https://doi.org/10.3390/M1842 - 25 Jun 2024
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Abstract
The title compound was synthesized from perfluoro-1-ethyltetralin and 1,2,3,4-tetrafluorobenzene under the action of antimony pentafluoride as a mixture of cis- and trans-isomers in a 71% isolated yield. The structure and cis-/trans-configuration of the isomers were determined by NMR [...] Read more.
The title compound was synthesized from perfluoro-1-ethyltetralin and 1,2,3,4-tetrafluorobenzene under the action of antimony pentafluoride as a mixture of cis- and trans-isomers in a 71% isolated yield. The structure and cis-/trans-configuration of the isomers were determined by NMR (19F, 13C), 19F–19F COSY, and 19F–19F NOESY 2D NMR spectroscopy. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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31 pages, 4467 KiB  
Article
Carbonylation of Polyfluorinated 1-Arylalkan-1-ols and Diols in Superacids
by Siqi Wang, Yaroslav V. Zonov, Victor M. Karpov, Olga A. Luzina and Tatyana V. Mezhenkova
Molecules 2022, 27(24), 8757; https://doi.org/10.3390/molecules27248757 - 10 Dec 2022
Cited by 1 | Viewed by 2106
Abstract
We describe the carbonylation of a series of mono and dihydroxy derivatives of polyfluorinated alkylbenzenes and benzocycloalkenes with OH groups at benzylic positions using carbon monoxide in the presence of a superacid (TfOH, a TfOH–SbF5 mixture, or a FSO3H–SbF5 [...] Read more.
We describe the carbonylation of a series of mono and dihydroxy derivatives of polyfluorinated alkylbenzenes and benzocycloalkenes with OH groups at benzylic positions using carbon monoxide in the presence of a superacid (TfOH, a TfOH–SbF5 mixture, or a FSO3H–SbF5 mixture). It was shown that the superacid-catalyzed addition of CO to various primary and secondary polyfluorinated alcohols and diols gives the corresponding mono- and dicarboxylic acids or lactones. The efficiency of various superacids depending on alcohol structure was evaluated, and FSO3H–SbF5 yielded the best results in most transformations. The addition of CO to secondary 1-arylalkan-1-ols containing vicinal fluorine atoms was found to be accompanied by elimination of HF with the formation of α,β-unsaturated aryl-carboxylic acids. In contrast to primary and secondary alcohols, conversion of tertiary perfluoro-1,1-diarylalkan-1-ols into carbonylation products is not complete, and the resulting carboxylic acids are easily decarboxylated after water treatment of the reaction mixture. Full article
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