Abstract
AbstractKetocalix[n]arenes can be prepared via oxidation of the methylene groups of protected calix[n]arenes. The presence of carbonyl groups at the bridges alters the preferred conformation and reactivity of the macrocycle and provides an entry point (via nucleophilic additions reactions) to a wide array of methylene-substituted derivatives as well as calix[n]radialenes.1 Introduction2 Synthesis of Ketocalix[n]arenes2.1 Ketocalix[4]arene Derivatives2.2 Systems Possessing both Carbonyl and Bromomethane Bridges2.3 Pentaoxoketocalix[5]arene and Hexaoxoketocalix[6]arene Derivatives2.4 Monooxo- and Dioxoketocalix[6]arenes3 Conformation of Ketocalixarenes4 Reactions of Ketocalixarenes4.1 Alkylation of the OH Groups4.2 Intramolecular Aromatic Nucleophilic Substitution4.3 Reduction of the Carbonyl Groups4.4 Reaction of 5c with PhLi4.5 Reaction with tert-Butyllithium5 From Ketocalix[n]arenes to Calix[n]radialenes and Calix[n]rotanes6 Summary and Outlook
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