By the same authors

From the same journal

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

Research output: Contribution to journalArticle

Published copy (DOI)

Author(s)

Department/unit(s)

Publication details

JournalNEW JOURNAL OF CHEMISTRY
DateAccepted/In press - 3 Sep 2018
DatePublished (current) - 3 Sep 2018
Issue number20
Volume42
Number of pages7
Pages (from-to)16646-16652
Original languageEnglish

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.

Discover related content

Find related publications, people, projects, datasets and more using interactive charts.

View graph of relations