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Unexpected cleavage of upper rim-bridged calix[4]arenes leading to linear oligophenolic derivatives

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Abstract

Regioselective meta-mercuration followed by Pd-catalysed intramolecular bridging gave birth to a novel type of calixarene bearing a single bond bridge between the meta positions of the neighboring aromatic subunits. These bridged derivatives possess extremely distorted cavities that imply possible amended properties over common calix[4]arenes. This new type of calixarene reactivity can be documented by acid-/electrophile-mediated cleavage of the basic macrocyclic skeleton leading to open oligomeric structures—the behavior of which has never been observed before in classic calix[4]arenes bearing alkoxy groups on the lower rim.

Graphical abstract: Unexpected cleavage of upper rim-bridged calix[4]arenes leading to linear oligophenolic derivatives

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Publication details

The article was received on 14 Dec 2017, accepted on 04 Jan 2018 and first published on 04 Jan 2018


Article type: Paper
DOI: 10.1039/C7OB03101G
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Unexpected cleavage of upper rim-bridged calix[4]arenes leading to linear oligophenolic derivatives

    P. Slavík, H. Dvořáková, M. Krupička and P. Lhoták, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C7OB03101G

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