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

P. Slavík; H. Dvořáková; M. Krupička; P. Lhoták

doi:10.1039/c7ob03101g

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

Chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	838-843
Number of pages	6
Journal	Organic and Biomolecular Chemistry
Volume	16
Issue number	5
Early online date	4 Jan 2018
DOIs	https://doi.org/10.1039/c7ob03101g
Publication status	E-pub ahead of print - 4 Jan 2018

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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.",

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AU - Slavík, P.

AU - Dvořáková, H.

AU - Krupička, M.

AU - Lhoták, P.

PY - 2018/1/4

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AB - 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.

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EP - 843

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 5

ER -

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

Abstract

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