TY - JOUR
T1 - Autoaccelerative diazo coupling with calix[4]arene
T2 - Substituent effects on the unusual co-operativity of the OH groups
AU - Shinkai, Seiji
AU - Araki, Koji
AU - Shibata, Jiro
AU - Tsugawa, Daisuke
AU - Manabe, Osamu
PY - 1990
Y1 - 1990
N2 - 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+.
AB - 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+.
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U2 - 10.1039/p19900003333
DO - 10.1039/p19900003333
M3 - Article
AN - SCOPUS:37049066820
SP - 3333
EP - 3337
JO - Journal of the Chemical Society, Perkin Transactions 2
JF - Journal of the Chemical Society, Perkin Transactions 2
SN - 1472-7781
IS - 12
ER -