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Transesterification of dialkyl carbonates with fluorine-containing alcohols

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Abstract

Reactions of transesterification of dimethyl, diethyl and dibutyl carbonates with 2,2,3,3-tetrafluoroethyl-, 2,2,3,3,4,4,5,5-octafluorobutyl- and 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorohexyl-carbinols were investigated in the presence of various catalysts. It was found that the conversion of starting dialkyl carbonate increases upon increasing the length of fluorine-containing radical in the presence of sodium alkoxide. It was shown that the maximum conversion of dimethyl carbonate (90%) was achieved in its reaction with 2,2,3,3,4,4,5,5-octafluoropentan-1-ol upon using catalysts such as K2CO3, NaOH, and sodium alkoxide. To achieve similar values of the conversion, Ti(OEt)4 and Ti(OiPr)4 should be used in the cases of diethyl and dibutyl carbonates, respectively.

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Authors and Affiliations

  1. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 ul. Sof’i Kovalevskoy, 620108, Ekaterinburg, Russian Federation

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

  2. Ural Federal University named after the First President of Russia, B. N. Yeltsin, 19 ul. Mira, 620002, Ekaterinburg, Russian Federation

    M. I. Kodess & A. V. Pestov

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

Correspondence to A. M. Semenova.

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Dedicated to Academician of the Russian Academy of Sciences V. N. Charushin on the occasion of his 70th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 933–936, May, 2021.

This work was carried out within the framework of the State Assignment to the I. Ya. Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences (Topic Nos AAAA-A19-119012290116-9 and AAAA-A19-119012490006-1) using the equipment of the Center for Joint Use “Spectroscopy and Analysis of Organic Compounds”.

This paper does not contain descriptions of studies on animals or humans.

The authors declare no competing interests.

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Semenova, A.M., Pervova, M.G., Ezhikova, M.A. et al. Transesterification of dialkyl carbonates with fluorine-containing alcohols. Russ Chem Bull 70, 933–936 (2021). https://doi.org/10.1007/s11172-021-3169-4

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  • DOI: https://doi.org/10.1007/s11172-021-3169-4

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