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

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F19%3A43919835" target="_blank" >RIV/60461373:22310/19:43919835 - isvavai.cz</a>
Result on the web
<a href="https://pubs.rsc.org/en/content/articlepdf/2019/ra/c9ra05075b" target="_blank" >https://pubs.rsc.org/en/content/articlepdf/2019/ra/c9ra05075b</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/c9ra05075b" target="_blank" >10.1039/c9ra05075b</a>

Result language
angličtina
Original language name
Synthesis of upper rim-double-bridged calix[4]arenes bearing seven membered rings and related compounds
Original language description
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 H-1 NMR titration experiments. The absolute configuration of the phenyl-substituted enantiomer (meta/meta-) was confirmed by single crystal structure determination (X-ray).
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry

Project
<a href="/en/project/GC18-08680J" target="_blank" >GC18-08680J: The synthesis and exploration of chromogenic and fluorogenic chiral calixarenes and related compounds</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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