Diazo coupling between calix[4]arene and p-nitrobenzenediazonium ion selectively afforded the tetrasubstituted calix[4]arene and almost no mono-, di-, and tri-substituted calix[4]arenes even in the presence of unchanged calix[4]arene: the unusual all-or-nothing substitution is attributed to the specific hydrogen-bonding effect among the calixarene OH groups.
S. Shinkai, K. Araki, J. Shibata and O. Manabe, J. Chem. Soc., Perkin Trans. 1, 1989, 195 DOI: 10.1039/P19890000195
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