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. ORCID: https://orcid.org/0000-0001-8821-0851 (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). pp. 994-1002. ISSN 1369-9261

Full text not available from this repository. (Request a copy)

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
UEA Research Groups:	Faculty of Science > Research Groups > Chemical Biology and Medicinal Chemistry (former - to 2021) Faculty of Science > Research Groups > Medicinal Chemistry (former - to 2017)
Depositing User:	Rachel Smith
Date Deposited:	16 Mar 2011 16:14
Last Modified:	04 May 2024 00:42
URI:	https://ueaeprints.uea.ac.uk/id/eprint/26432
DOI:	10.1039/b714735j

Actions (login required)

View Item