Intramolecular etherification of five-membered cyclic carbonates bearing hydroxyalkyl groupsElectronic supplementary information (ESI) available: additional spectroscopic, and crystallographic data. CCDC numbers 868593-868594. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c2gc35265f

• Main Authors: Tomczyk, Karolina M, Gu ka, Piotr A, Parzuchowski, Pawe G, Zachara, Janusz, Rokicki, Gabriel
• Format: Article
• Language: English
• ISSN: 1463-9262; 1463-9270
• DOI: 10.1039/c2gc35265f

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. We report a one-pot synthetic route to tetrahydrofuran derivatives, which were unexpectedly produced under basic conditions by intramolecular etherification of substituted five-membered cyclic carbonates.