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Issue 6, 2012
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Intramolecular etherification of five-membered cyclic carbonates bearing hydroxyalkyl groups

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Abstract

We report a new one-pot synthetic route to tetrahydrofuran derivatives, which were unexpectedly produced under basic conditions by intramolecular etherification of substituted five-membered cyclic carbonates. For alcohols with vicinal hydroxyl groups, and additional OH groups at the β-position, intramolecular etherification leading to 3-hydroxytetrahydrofuran derivatives was observed. These reactions were studied for compounds having from 2 to 6 hydroxyl groups per molecule, and the mechanism was proposed. The developed method provides a new environmentally friendly approach to the synthesis of five-membered cyclic ether derivatives under non-acidic conditions.

Graphical abstract: Intramolecular etherification of five-membered cyclic carbonates bearing hydroxyalkyl groups

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Publication details

The article was received on 21 Feb 2012, accepted on 28 Mar 2012 and first published on 02 Apr 2012


Article type: Paper
DOI: 10.1039/C2GC35265F
Citation: Green Chem., 2012,14, 1749-1758
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    Intramolecular etherification of five-membered cyclic carbonates bearing hydroxyalkyl groups

    K. M. Tomczyk, P. A. Guńka, P. G. Parzuchowski, J. Zachara and G. Rokicki, Green Chem., 2012, 14, 1749
    DOI: 10.1039/C2GC35265F

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