p-tert-Butylcalixarene was attempted to O-alkylate with alcohols and diols under the Mitsunobu protocol. Regio-and conformation-selective reactions were not observed with alcohols and oligoethylene glycols, but 1,6-hexaneand 1,8-octanediols effected cone-selective A,D-bridging. Exhaustive alkylation of the remaining four OH groups in a cyclized molecule was carried out under base-promoted conditions and the conformation of the products along with the metal ion binding properties were studied by NMR methods.
Keywords: Calixarene, Mitsunobu cyclization, O-Alkylation, Conformation, Cation binding
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