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meta-Bridged calix[4]arenes with the methylene moiety possessing in/out stereochemistry of substituents

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Abstract

meta-Substituted organomercury calix[4]arenes and their corresponding iodo derivatives have been used for lithiation followed by a reaction with various aldehydes or ketones. The resulting diastereomers were in some cases separable using simple column chromatography. Subsequent intramolecular Friedel–Crafts alkylation led to calix[4]arenes with an additional methylene bridge bearing two different substituents with in/out (relative to the cavity) stereochemistry. Our results indicate that the stereochemistry of the final cyclised product does not depend on the structure/stereochemistry of the starting compound, but rather it is influenced by the stability of the products. The relationship between the positions of these substituents and the complexation properties was demonstrated by 1H NMR titration experiments with N-methylpyridinium iodide.

Graphical abstract: meta-Bridged calix[4]arenes with the methylene moiety possessing in/out stereochemistry of substituents

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Publication details

The article was received on 24 May 2018, accepted on 03 Sep 2018 and first published on 03 Sep 2018


Article type: Paper
DOI: 10.1039/C8NJ02577K
Citation: New J. Chem., 2018, Advance Article
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    meta-Bridged calix[4]arenes with the methylene moiety possessing in/out stereochemistry of substituents

    P. Slavík, V. Eigner and P. Lhoták, New J. Chem., 2018, Advance Article , DOI: 10.1039/C8NJ02577K

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