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Synthesis of Strained Macrocyclic Biaryls for Enthalpy-Driven Ring-Opening Polymerization

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posted on 13.12.2005, 00:00 by Howard M. Colquhoun, Zhixue Zhu, Christopher C. Dudman, Caroline A. O'Mahoney, David J. Williams, Michael G. B. Drew
Polymerizable macrocyclic biarylene−ether−ketones and biarylene−ether−sulfones are accessible from linear, bis(chloro)-terminated oligomers via nickel-catalyzed, intramolecular coupling under pseudo-high-dilution conditions. Single-crystal X-ray analyses of the resulting cyclo-oligomers reveal extremely distorted and highly strained geometries, with 4,4‘-biphenylene units showing deviations of up to 70° from linearity.