The regioselective mercuration of tetraalkylated calix[4]arenes with Hg(OCOCF3)2 leads to the formation of meta-substituted products which enabled Pd-catalysed intramolecular bridging within the calixarene skeleton. Bridged derivatives represent a completely novel substitution pattern in calixarene chemistry with extremely distorted cavities and possible applications in supramolecular chemistry.

Department of Organic Chemistry Institute of Chemical Technology Prague Technicka 5 166 28 Prague 6 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

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