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Appending aromatic moieties at the para- and meta-position of calixarene phenol rings via p-bromodienone route
Authors:Francesco Troisi  Michele Carratù
Institution:Dipartimento di Chimica, Università di Salerno, Via Ponte don Melillo, I-84088 Fisciano, Salerno, Italy
Abstract:The silver-mediated nucleophilic substitution on calixarene p-bromodienone derivatives (the ‘p-bromodienone route’) with activated aromatic substrates allows the introduction of aromatic moieties at the para- or meta-position of calixarene aromatic rings. Less reactive substrates mainly afford C-O para-coupled derivatives, while more activated ones mainly give inherently chiral, C-C meta-coupled products through a dienone-phenol rearrangement of the intermediate dienone derivative. Examples of C-C para-coupling and O-C coupling at the endo calixarene oxygen atom were also observed.
Keywords:Calixarene exo-rim  p-Bromodienone route  Inherently chiral calixarenes  Dienone-phenol rearrangement  Meta-substituted calixarenes
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