Summary
Partial elucidation of the mechanism of polymerization of 4,4′-difluorodiphenylether by reaction with n-butyllithium to poly-oxy-biphenyl and polyoxy-biphenylene is described. It could be afforded after considering the results of trapping experiments using carbon dioxide, water, deuterium oxide or fur an. The intermediates of the first steps of the reaction are proposed. IR, NMR, and mass spectra of different derivatives suggest a complex reaction mechanism with the participation of different species, involving metalation reactions of 4,4′-difluorodiphenylether, elimination toward dehydroaromatic species with nucleophilic addition reactions and elimination of lithium fluoride leading to both biphenylic and biphenylenic structures. These polymers showed outstanding properties, particularly those common to aromatic polymers such as great thermal stability.
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de la Fuente, J.R., Martínez de Bertorello, M. & Bertorello, H.E. Polymerization of 4,4′-difluorodiphenylether by reaction with n-butyllithium. Polymer Bulletin 13, 557–563 (1985). https://doi.org/10.1007/BF00263478
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DOI: https://doi.org/10.1007/BF00263478