Autoaccelerative diazo coupling with calix[4]arene: Substituent effects on the unusual co-operativity of the OH groups

Seiji Shinkai, Koji Araki, Jiro Shibata, Daisuke Tsugawa, Osamu Manabe

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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+.

Original languageEnglish
Pages (from-to)3333-3337
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number12
Publication statusPublished - Dec 1 1990

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All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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