Autoaccelerative diazo coupling with calix[4]arene: substituent effects on the unusual co-operativity of the OH groups
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 12,p. 3333-3337
- https://doi.org/10.1039/p19900003333
Abstract
Diazo coupling between calix[4]arene and five substituted benzenediazonium ions in tetrahydrofuran at 5 °C in the presence of pyridine afforded the tetrasubstituted calix[4]arenes as main products and small amounts of mono-, di- and tri-substituted calix[4]arenes even in the presence of unchanged calix[4]arene: the unusual autoaccelerative substitution reaction is attributed to the specific hydrogen-bonding effect among the calix[4]arene OH groups. The products were applied as new ‘chromophoric calix[4]arenes’, which selectively recognised Li+.Keywords
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