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

P. Slavík, H. Dvořáková, V. Eigner, P. Lhoták*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)14738-14745
Number of pages8
JournalNEW JOURNAL OF CHEMISTRY
Volume41
Issue number23
DOIs
Publication statusPublished - 2 Nov 2017

Cite this