Journal
TETRAHEDRON
Volume 68, Issue 24, Pages 4757-4764Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.04.009
Keywords
Crown ether; Molecular clips; Diphenylglycoluril; Extraction; Crystal structure
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A convenient method for the synthesis of a series of molecular clips based on the diphenylglycoluril framework and benzocrown ether moieties by the reaction of bis(cyclomethoxymethylene)diphenylglycoluril with benzocrown ethers in polyphosphoric acid is proposed. X-ray diffraction analysis of molecular clips with the benzo-12-crown-4 and benzo-15-crown-5 fragments showed that both compounds are chloroform solvates with the stoichiometry clip:chloroform 1:1. By theoretical and experimental methods the existence of obtained clips in an anti-anti conformation was proved. The complexation properties of the obtained molecular clips were examined toward alkali metal and ammonium ions by FABMS spectrometry and extraction experiments. (C) 2012 Elsevier Ltd. All rights reserved.
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