Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Stereochemistry and Recognition Properties of Calixarenes
Koji ARAKI
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1995 Volume 53 Issue 1 Pages 22-31

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Abstract
The conformational changes among several conformational isomers of calix [4] arenes can take place because the OH groups rotate through the annulus. This inversion was inhibited by the introduction of the substituents bulkier than ethyl group into the OH groups and the resulting conformational isomers were separated. The selective syntheses of all partially O-propylated compounds and conformational isomers in p-tert-butylcalix [4] arene were successful by the combination of protection-deprotection method and the optimization of the reaction conditions (base, temperature, solvent, etc). Several of these compounds can possess the chirality which is caused by the disappearance of the symmetries on the conformation or based on the order in the array of different substituents. We succeeded in the syntheses and the optical resolutions of these calixarenes with molecular chirality for the first time.
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© The Society of Syhthetic Organic Chemistry, Japan
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