Journal
TETRAHEDRON
Volume 58, Issue 19, Pages 3729-3736Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(02)00342-3
Keywords
calix[4]arenes; methylene bridges; receptor polycavities
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Chloromethylation of 5,17-di-tert-butyl-25,27-dihydroxy-26,28-dimethoxycalix[4]arene with chloromethyl methyl ether in the presence of zinc chloride led to the formation of macrocyclic and linear oligomers containing three to five calix[4]arenes bridged via methylenes at the upper rims. Under the identical conditions, however, 5,17-di-tert-amyl-25,27-dihydroxy-26,28-dimethoxycalix[4]arene was converted into a mixture of linear dimer and trimer in yields of 39.5 and 34%, respectively. Only dimer was obtained as the sole product in 41% yield when 25,27-dihydroxy-26,28-diethoxycalix[4]arene was used. Efficient synthesis of linear or starlike polycalixarenes was achieved utilizing the Friedel-Crafts reaction of debutylated or partially debutylated calix[4]arenes with chloromethylated calix[4]arene promoted by anhydrous zinc chloride. (C) 2002 Elsevier Science Ltd. All rights reserved.
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