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

Research output: Contribution to journalArticlepeer-review


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 languageEnglish
Pages (from-to)16646-16652
Number of pages7
Issue number20
Publication statusPublished - 3 Sept 2018

Cite this