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meta-Bridged calix[4]arenes prepared by Friedel–Crafts alkylation

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Abstract

By applying electrophilic aromatic mercuration of calix[4]arene the introduction of substituted hydroxymethyl groups at the meta position of the basic skeleton has been achieved. Subsequent intramolecular Friedel–Crafts alkylation led to a novel type of bridged calix[4]arenes with additional symmetrically substituted methylene bridges connecting to the neighbouring aromatic units. Additionally, this new efficient synthetic pathway was also used for the preparation of a double bridged analogue. These compounds with rigidified cavities can complex cations and neutral compounds using CH–π and/or cation–π interactions as demonstrated by 1H NMR titration experiments.

Graphical abstract: meta-Bridged calix[4]arenes prepared by Friedel–Crafts alkylation

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Publication details

The article was received on 07 Sep 2017, accepted on 02 Nov 2017 and first published on 02 Nov 2017


Article type: Paper
DOI: 10.1039/C7NJ03394J
Citation: New J. Chem., 2017, Advance Article
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    meta-Bridged calix[4]arenes prepared by Friedel–Crafts alkylation

    P. Slavík, H. Dvořáková, V. Eigner and P. Lhoták, New J. Chem., 2017, Advance Article , DOI: 10.1039/C7NJ03394J

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