Synthesis of new aromatic perfluorovinyl ether monomers containing phosphonic acid functionality |
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Authors: | Renaud Souzy Bernard Boutevin |
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Affiliation: | a Laboratory of Macromolecular Chemistry, UMR (CNRS) 5076, Ecole Nationale Supérieure de Chimie de Montpellier, 8 Rue Ecole Normale, 34296 Montpellier Cedex 5, France b Laboratory of Organic Chemistry, UMR (CNRS) 5076, Ecole Nationale Supérieure de Chimie de Montpellier, 8 Rue Ecole Normale, 34296 Montpellier Cedex 5, France |
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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 , and NMR, mass spectrometry (EI), and by FTIR. |
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Keywords: | [(α,β,β-Trifluorovinyl)oxy]benzene phosphonic acid Michaelis-Arbuzov reaction Michaelis-Becker reaction Palladium catalyst Nuclear magnetic resonance Fluoromonomers |
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