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

P. Slavík, H. Dvořáková, M. Krupička, P. Lhoták*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


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.

Original languageEnglish
Pages (from-to)838-843
Number of pages6
JournalOrganic and Biomolecular Chemistry
Issue number5
Early online date4 Jan 2018
Publication statusE-pub ahead of print - 4 Jan 2018

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