Issue 6, 2008
From the journal:

New Journal of Chemistry

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

Deborah Moore,a   Graeme W. Watson,a   Thorfinnur Gunnlaugsson*a  and  Susan E. Matthews*b  

* Corresponding authors

a School of Chemistry, Trinity College, University of Dublin, Dublin 2, Ireland
E-mail: gunnlaut@tcd.ie

b School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich, UK
E-mail: susan.matthews@uea.ac.uk
Fax: 44 1603-592003
Tel: 44 1603 595986

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.

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

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Article information

DOI
https://doi.org/10.1039/B714735J
Article type
Paper
Submitted
25 Sep 2007
Accepted
10 Jan 2008
First published
04 Feb 2008

New J. Chem., 2008,32, 994-1002

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

D. Moore, G. W. Watson, T. Gunnlaugsson and S. E. Matthews, New J. Chem., 2008, 32, 994 DOI: 10.1039/B714735J

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