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Transesterification of Diethyl Carbonate with Methanol Catalyzed by Sodium Methoxide

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Abstract

The mechanism of sodium methoxide-catalyzed transesterification of diethyl carbonate with metha-nol to dimethyl carbonate has been studied by DFT quantum chemical calculations using B3LYP functional. Ethoxy groups in the substrate are replaced successively through four-coordinate carbon intermediates which undergo decomposition. Sodium methoxide with carbonates forms pre-reaction complexes where the sodium cation is coordinated to the carbonate fragment. These complexes are characterized by enhanced electron-donating power of the methoxy fragment and increased electron-withdrawing power of the carbonate fragment, which favors the transesterification process.

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Authors and Affiliations

  1. Kazan National Research Technological University, Kazan, Tatarstan, Russia

    A. Ya. Samuilov, M. V. Korshunov & Ya. D. Samuilov

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  1. A. Ya. Samuilov
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  2. M. V. Korshunov
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Correspondence to A. Ya. Samuilov.

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Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 9, pp. 1426–1432.

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Samuilov, A.Y., Korshunov, M.V. & Samuilov, Y.D. Transesterification of Diethyl Carbonate with Methanol Catalyzed by Sodium Methoxide. Russ J Org Chem 55, 1338–1343 (2019). https://doi.org/10.1134/S1070428019090124

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  • DOI: https://doi.org/10.1134/S1070428019090124

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