Bridge-substituted calix[4]arenes: syntheses, conformations and application

Fischer, Conrad, Gruber, Tobias, Seichter, Wilhelm and Weber, Edwin (2011) Bridge-substituted calix[4]arenes: syntheses, conformations and application. Organic & Biomolecular Chemistry, 9 (11). pp. 4347-4352. ISSN 1477-0520

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Bridge-substituted calix[4]arenes: syntheses, conformations and application

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The bridge-substituted calix[4]arene carboxylic acid, 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetramethoxy-calix[4]arene-2-carboxylic acid (1), can be readily converted to various esters 2-4 and reduced to the alcohol 5, which reacts with methyl iodide to give the ether 6. The alcohol can be dansylated to give 7, the fluorescence of which is selectively quenched by Cu(II) in acetonitrile. An attempt to convert the acid 1 to an amide resulted unexpectedly in the formation of a lactone 8. The conformational characteristics of 1-8 have been studied in solution and, in the cases of 2 and 4, in the solid state by determination of their single-crystal X-ray structures. With the exception of 8, in all these compounds the bridge substituent adopts an equatorial (lateral) orientation.

Keywords:calixarene, cyclophane, X-ray diffraction, organic synthesis, Molecular Conformation
Subjects:F Physical Sciences > F131 Crystallography
F Physical Sciences > F160 Organic Chemistry
F Physical Sciences > F130 Structural Chemistry
Divisions:College of Science > School of Pharmacy
ID Code:20025
Deposited On:15 Jan 2016 10:55

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