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Synthesis of Polyfluorinated Tetraoxacalix[4]arenes by Reaction of Pentafluoronitrobenzene with Resorcinol, Orcinol, and Tetrafluororesorcinol

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Abstract

Successive reactions of pentafluoronitrobenzene with resorcinol, orcinol, and tetrafluororesorcinol in acetonitrile in the presence of triethylamine afforded polyfluorinated ABAB and ABAC tetraoxacalix[4]arenes. Analysis of the1H and 19F NMR spectra of the synthesized oxacalixarenes indicated high conformational mobility of the resorcinol and tetrafluororesorcinol fragments of their molecules due to interaction with the solvent.

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ACKNOWLEDGMENTS

The authors thank the Joint Chemical Service Center, Siberian Branch, Russian Academy of Sciences, for providing facilities for analytical and spectral studies.

Funding

H. Han thanks the State Fellowship Committee of the People Republic of China for financial support.

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Correspondence to V. N. Kovtonyuk.

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Kovtonyuk, V.N., Han, H. & Gatilov, Y.V. Synthesis of Polyfluorinated Tetraoxacalix[4]arenes by Reaction of Pentafluoronitrobenzene with Resorcinol, Orcinol, and Tetrafluororesorcinol. Russ J Org Chem 56, 1153–1159 (2020). https://doi.org/10.1134/S1070428020070052

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  • DOI: https://doi.org/10.1134/S1070428020070052

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