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

0510558 - FZÚ 2020 RIV GB eng J - Journal Article
Slavík, P. - Eigner, Václav - Lhoták, P.
meta-Bridged calix[4]arenes with the methylene moiety possessing in/out stereochemistry of substituents.
New Journal of Chemistry. Roč. 42, č. 20 (2018), s. 16646-16652. ISSN 1144-0546. E-ISSN 1369-9261
Institutional support: RVO:68378271
Keywords : meta-substituted organomercury * lithiation * crystal structure * alkylation * methylene bridges
OECD category: Condensed matter physics (including formerly solid state physics, supercond.)
Impact factor: 3.069, year: 2018
Method of publishing: Limited access
https://doi.org/10.1039/c8nj02577k

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 stereochemistry. Our results indicate that the stereochemistry of the final cyclised product does not depend on the structure/stereochemistry of the starting compound, but rath er it is influenced by the stability of the products.
Permanent Link: http://hdl.handle.net/11104/0301005