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

P. Slavík; V. Eigner; P. Lhoták

doi:10.1039/c8nj02577k

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

P. Slavík, V. Eigner, P. Lhoták^*

^*Corresponding author for this work

Chemistry

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

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.

Original language	English
Pages (from-to)	16646-16652
Number of pages	7
Journal	NEW JOURNAL OF CHEMISTRY
Volume	42
Issue number	20
DOIs	https://doi.org/10.1039/c8nj02577k
Publication status	Published - 3 Sept 2018

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AU - Slavík, P.

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

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