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New Synthetic Approach to Polyfluorinated Carbonates

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Abstract

Transesterification of commercial titanium(IV) alkoxides with 2,2,3,3-tetrafluoropropan-1-ol, followed by in situ transesterification of mixed titanium(IV) alkoxides thus formed with diphenyl carbonate, afforded alkyl 2,2,3,3-tetrafluoropropyl carbonates and bis(2,2,3,3-tetrafluoropropyl) carbonate in up to 60% yield. The degree of transesterification decreased in the series (i-PrO)4Ti > (EtO)4Ti > (BuO)4Ti and did not exceed 68%. The selectivity for alkyl 2,2,3,3-tetrafluoropropyl carbonates and bis(2,2,3,3-tetrafluoropropyl) carbonate was found to change depending on the composition of mixed titanium(IV) alkoxide formed in situ.

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ACKNOWLEDGMENTS

The spectral and analytical data were obtained using the facilities of the Spectroscopy and Analysis of Organic Compounds joint center.

Funding

This study was performed in the framework of state task to the Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences (project nos. AAAA-A19-119012490006-1, AAAA-A19-119012290116-9).

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Authors and Affiliations

  1. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 620990, Yekaterinburg, Russia

    A. M. Semenova, M. A. Ezhikova, M. I. Kodess, A. Ya. Zapevalov & A. V. Pestov

  2. Yeltsin Ural Federal University, 620002, Yekaterinburg, Russia

    M. I. Kodess & A. V. Pestov

Authors
  1. A. M. Semenova
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  2. M. A. Ezhikova
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  3. M. I. Kodess
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  4. A. Ya. Zapevalov
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  5. A. V. Pestov
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Corresponding author

Correspondence to A. V. Pestov.

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Semenova, A.M., Ezhikova, M.A., Kodess, M.I. et al. New Synthetic Approach to Polyfluorinated Carbonates. Russ J Org Chem 56, 645–648 (2020). https://doi.org/10.1134/S1070428020040120

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  • DOI: https://doi.org/10.1134/S1070428020040120

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