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Nucleophilic addition to acetylenes in superbasic catalytic systems: XVII. Vinyl ethers with furyl and cycloacetal fragments: Synthesis and structure

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Abstract

4-Hydroxymethyl-2-(2-furyl)-1,3-dioxolane and 5-hydroxy-2-(2-furyl)-1,3-dioxane consisting of mixtures of cis- and trans-isomers react with acetylene in the superbasic catalytic system KOHH-DMSO at the atmospheric or higher pressure (80–85°C, 2–3 h) giving the corresponding vinyl ethers in 88–90% yield. The ratio of the structural and configurational isomers in vinyl ethers remains the same as in the initial compounds.

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Authors and Affiliations

  1. Faworsky Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, Irkutsk, 664033, Russia

    L. A. Oparina, O. V. Vysotskaya, A. V. Stepanov, N. K. Gusarova, K. A. Chernyshev, L. B. Krivdin & B. A. Trofimov

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  1. L. A. Oparina
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  2. O. V. Vysotskaya
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  3. A. V. Stepanov
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  4. N. K. Gusarova
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  5. K. A. Chernyshev
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  6. L. B. Krivdin
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  7. B. A. Trofimov
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Corresponding author

Correspondence to B. A. Trofimov.

Additional information

Original Russian Text © L. A. Oparina, O. V. Vysotskaya, A. V. Stepanov, N. K. Gusarova, K. A. Chernyshov, L. B. Krivdin, and B. A. Trofimov, 2010, published in Zhurnal Organicheskoi Khimii, 2010, Vol. 46, No. 9, pp. 1380–1384.

For Communication XVI, see [1].

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Oparina, L.A., Vysotskaya, O.V., Stepanov, A.V. et al. Nucleophilic addition to acetylenes in superbasic catalytic systems: XVII. Vinyl ethers with furyl and cycloacetal fragments: Synthesis and structure. Russ J Org Chem 46, 1383–1387 (2010). https://doi.org/10.1134/S1070428010090204

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  • DOI: https://doi.org/10.1134/S1070428010090204

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