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

0510509 - FZÚ 2020 RIV GB eng J - Journal Article
Slavík, P. - Dvořáková, H. - Eigner, Václav - Lhoták, P.
meta-Bridged calix[4] arenes prepared by Friedel-Crafts alkylation.
New Journal of Chemistry. Roč. 41, č. 23 (2017), s. 14738-14745. ISSN 1144-0546. E-ISSN 1369-9261
Institutional support: RVO:68378271
Keywords : electrophilic aromatic mercuration * hydroxymethyl groups * methylene bridges * crystal structure
OECD category: Condensed matter physics (including formerly solid state physics, supercond.)
Impact factor: 3.201, year: 2017
Method of publishing: Limited access
https://doi.org/10.1039/c7nj03394j

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–pπ and/or cation–π interactions as demonstrated by 1H NMR titration experiments.
Permanent Link: http://hdl.handle.net/11104/0300975