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

Deborah Moore, Graeme W. Watson, Thorfinnur Gunnlaugsson, Susan E Matthews

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10 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)994
Number of pages1
JournalNew Journal of Chemistry
Volume32
Issue number6
DOIs
Publication statusPublished - 2008

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