Dimercuration of calix[4]arenes: novel substitution pattern in calixarene chemistry
Karolína Flídrová1, Stanislav Böhm, Hana Dvořáková
1Department of Organic Chemistry, ‡Laboratory of NMR Spectroscopy, and §Department of Solid State Chemistry. Prague Institute of Chemical Technology (PICT) , Technicka 6, 166 28 Prague 6, Czech Republic.
Abstract:
A mercuration reaction of tetrapropoxycalix[4]arene immobilized in the cone conformation gave a mixture of two dimercurated products (meta,meta and meta,para) in approximately a 1:1 ratio. Both regioisomers represent inherently chiral compounds, which makes them very attractive for design of novel receptors. As demonstrated by Pd-catalyzed arylation, the different reactivity of HgCl functions in the meta,para-disubstituted isomer opens the door for regioselective introductions of two different functional groups to achieve a substitution pattern so far unknown in calixarene chemistry.
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