Issue 38, 2019

Synthesis of upper rim-double-bridged calix[4]arenes bearing seven membered rings and related compounds

Abstract

Meta/meta- and meta/para-disubstituted organomercury calix[4]arenes in the cone conformation were transformed into corresponding amino derivatives. Acylation and subsequent intramolecular cyclization using the Bischler–Napieralski reaction provided, in the case of the meta/meta-series, double bridged calixarenes possessing seven membered rings on the upper rim. A similar synthetic strategy applied to meta/para-isomers allowed for the isolation of monobridged compounds bearing an additional trifluoroacetamido group located distally to seven-membered rings. Both series represent inherently chiral systems, which were successfully resolved using preparative chiral HPLC. The pure enantiomers exhibited a recognition ability towards selected chiral guest molecules as documented by the 1H NMR titration experiments. The absolute configuration of the phenyl-substituted enantiomer (meta/meta-) was confirmed by single crystal structure determination (X-ray).

Graphical abstract: Synthesis of upper rim-double-bridged calix[4]arenes bearing seven membered rings and related compounds

Supplementary files

Article information

Article type
Paper
Submitted
04 Jul 2019
Accepted
05 Jul 2019
First published
16 Jul 2019
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2019,9, 22017-22030

Synthesis of upper rim-double-bridged calix[4]arenes bearing seven membered rings and related compounds

M. Tlustý, V. Eigner, M. Babor, M. Kohout and P. Lhoták, RSC Adv., 2019, 9, 22017 DOI: 10.1039/C9RA05075B

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