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Unprecedented Meta-Substitution of Calixarenes: Direct Way to Inherently Chiral Derivatives
- Slavik, Petr, Dudic, Miroslav, Flidrova, Karolina, Sykora, Jan, Cisarova, Ivana, Böhm, Stanislav, Lhotak, Pavel
- Organic letters 2012 v.14 no.14 pp. 3628-3631
- Lewis acids, aromatic hydrocarbons, chemical reactions, chemical structure, regioselectivity
- Electrophilic aromatic substitution in the calix[n]arene series is a well-established procedure leading exclusively to para-substituted derivatives. An unprecedented regioselectivity of the mercuration reaction leading to the meta-substituted calixarenes is described. These compounds represent a new type of substitution pattern in classical calixarene chemistry and open the door for the straightforward synthesis of inherently chiral receptors based on calixarenes.