Cyclization of p-tert-Butylcalix[6]arene with Diols Under the Mitsunobu Protocol. A Conformational Study of the Peralkylated Derivatives

Author(s): Alajos Grun, Barbara Balazs, Istvan Bitter.

Journal Name: Letters in Organic Chemistry

Volume 6 , Issue 4 , 2009

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Abstract:

p-tert-Butylcalix[6]arene 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: Calix[6]arene, Mitsunobu cyclization, O-Alkylation, Conformation, Cation binding

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Article Details

VOLUME: 6
ISSUE: 4
Year: 2009
Page: [311 - 315]
Pages: 5
DOI: 10.2174/157017809788489954
Price: $65

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