Chemistry of 2,14-Dithiacalix[4]arene: Alkylation and Conformational Behavior of Peralkylated Products

2,14-Dithiacalix­[4]­arene, prepared on a multigram scale, was alkylated using the reaction conditions well known from the chemistry of classical calixarenes or thiacalixarenes to study the specific conformational preferences and dynamic behavior of the corresponding tetraalkylated derivatives. As p...

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Published in:Journal of organic chemistry 2019-09, Vol.84 (18), p.11572-11580
Main Authors: Kortus, Daniel, Mikšátko, Jiří, Kundrát, Ondřej, Babor, Martin, Eigner, Václav, Dvořáková, Hana, Lhoták, Pavel
Format: Article
Language:English
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Summary:2,14-Dithiacalix­[4]­arene, prepared on a multigram scale, was alkylated using the reaction conditions well known from the chemistry of classical calixarenes or thiacalixarenes to study the specific conformational preferences and dynamic behavior of the corresponding tetraalkylated derivatives. As proved by the combination of the X-ray crystallography and dynamic NMR techniques, the presence of mixed bridges (−CH2– and −S– groups) within the basic skeleton brings about considerable changes in the mutual ratios of the individual conformers compared to the parent macrocycles. Interestingly, certain conformers, hardly accessible for common calixarenes/thiacalixarenes (e.g., 1,2-alternates) are easily prepared in very good yields in the case of 2,14-dithiacalix[4]­arene, which makes this mixed-bridge system attractive as molecular scaffold for supramolecular applications.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b01493