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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19 Citations (Scopus)


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)994-1002
Number of pages9
JournalNew Journal of Chemistry
Issue number6
Publication statusPublished - 2008

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