Selective formation of the rctt chair stereoisomers of octa-O-alkyl resorcin[4]arenes using Brønsted acid catalysis

Moore, Deborah, Watson, Graeme W., Gunnlaugsson, Thorfinnur and Matthews, Susan E (2008) Selective formation of the rctt chair stereoisomers of octa-O-alkyl resorcin[4]arenes using Brønsted acid catalysis. New Journal of Chemistry, 32 (6). p. 994. ISSN 1369-9261

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Abstract

New synthetic conditions are described for the fully selective formation of the rctt chair stereoisomers of octa-O-alkyl resorcin[4]arenes; these offer a clean route into the chair conformer of these interesting receptor molecules. Brønsted acid catalysis in acetic acid solutions results in the formation of the single isomer when 1,3-dimethoxybenzene is heated at 80 °C with a range of aldehydes, straight- and branched-chain or aromatic, and with an aldehyde synthon. An investigation of reaction conditions indicated that, in this case, the rctt chair stereoisomer was the thermodynamic product, a result confirmed by molecular modelling studies that show that this stereoisomer is of lower energy than the expected rccc boat stereoisomer.

Item Type: Article
Faculty \ School: Faculty of Science > School of Pharmacy
Related URLs:
Depositing User: Rachel Smith
Date Deposited: 16 Mar 2011 16:14
Last Modified: 21 Apr 2020 18:59
URI: https://ueaeprints.uea.ac.uk/id/eprint/26432
DOI: 10.1039/b714735j

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