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 calix[4]arenes 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.

Department of Organic Chemistry Prague Institute of Chemical Technology Technicka 6 166 28 Prague 6 Czech Republic Institute of Organic Chemistry and Biochemistry v v i Academy of Sciences of the Czech Republic Flemingovo 2 166 10 Prague 6 Czech Republic Institute of Chemical Process Fundamentals v v i Academy of Sciences of the Czech Republic Rozvojova 135 165 02 Prague 6 Czech Republic and Department of Inorganic Chemistry Charles University Hlavova 8 128 43 Prague 2 Czech Republic

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Upper rim-bridged calixarenes

Upper Rim-Bridged Calix[4]arenes via Cyclization of meta Alkynyl Intermediates with Diphenyl Diselenide

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