Article Dans Une Revue Journal of Fluorine Chemistry Année : 2004

Synthesis of new aromatic perfluorovinyl ether monomers containing phosphonic acid functionality

Résumé

Abstract The synthesis of a new perfluorovinyl ether monomer containing phosphonic acid functionality is reported. It started from 4-[(α,β,β-trifluorovinyl)oxy]bromo benzene prepared in two steps from the nucleophilic substitution of 4-bromophenate to 1,2-dibromotetrafluoroethane. The [(α,β,β-trifluorovinyl)oxy]benzene dialkyl phosphonate was prepared according to various methods of phosphonation like a Michaelis–Arbuzov or a Michaelis–Becker or a palladium catalysed arylation in the presence of various reactants. The influence of the nature of the method and of the reactants onto the yields is discussed. It was shown that reaction involving a palladium triphenyl phosphine catalyst led to the best yield. All different aromatic intermediates and fluoromonomers were characterised by 1H, 31P and 19F NMR, mass spectrometry (EI), and by FTIR.

Dates et versions

hal-00168195 , version 1 (24-08-2007)

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Renaud Souzi, Bruno Ameduri, Bernard Boutevin, David Null Virieux. Synthesis of new aromatic perfluorovinyl ether monomers containing phosphonic acid functionality. Journal of Fluorine Chemistry, 2004, 125 (9), pp.1317-1324. ⟨10.1016/j.jfluchem.2004.03.010⟩. ⟨hal-00168195⟩
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