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.
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Rearrangement of meta-Bridged Calix[4]arenes Promoted by Internal Strain.
J Org Chem
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Department of Organic Chemistry , University of Chemistry and Technology, Prague (UCTP) , Technická 5 , 166 28 Prague 6 , Czech Republic.
The meta-bridged calixarenes possess a rigidified and highly distorted cavity, where the additional single-bond bridge imposes an extreme internal strain on the whole system. As a consequence, these compounds exhibit a reasonably amended reactivity, compared with common calix[4]arene derivatives, which is governed by the release of internal strain. This can be documented by the reaction of the bridged calix[4]arene with PO or Nafion-H, leading (apart from polymers) to a macrocyclic product with a rearranged basic skeleton.
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Department of Organic Chemistry, Institute of Chemical Technology Prague (ICTP), Technicka 5, 166 28, Prague 6, Czech Republic.
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Department of Organic Chemistry, Institute of Chemical Technology Prague (ICTP), Technicka 5, 166 28, Prague 6, Czech Republic.
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.
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