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.

Department of Organic Chemistry ‡Laboratory of NMR Spectroscopy and §Department of Solid State Chemistry Prague Institute of Chemical Technology Technicka 6 166 28 Prague 6 Czech Republic

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Upper rim-bridged calixarenes

The Formation of Inherently Chiral Calix[4]quinolines by Doebner-Miller Reaction of Aldehydes and Aminocalixarenes

Synthesis of upper rim-double-bridged calix[4]arenes bearing seven membered rings and related compounds