Résumé
The synthesis of four fluorinated acrylates and methacrylates bearing a morpholino group in the lateral chain was achieved in four steps in very high yield: the radical addition of perfluoroalkyl iodides on to allyl acetate followed by an alkaline cyclization led to fluorinated epoxides. These compounds reacted with an excess of morpholine and yielded morpholinofluorinated alcohols that, condensed with acrylic or methacrylic anhydride, produced the expected fluorinated acrylic or methacrylic monomers, respectively. The behaviour in homopolymerization of such new olefins involved the study of the square of the propagation rate constant to the termination rate constant ratio (
k
p
2
k
te
) by two different methods. The poor reactivity of these monomers has been shown by a GC kinetic study and also by the calculation of the yield. The values of
k
p
2
k
te
show that they are two-hundred-times less reactive than usual fluorinated acrylic monomers. We finally propose a reactivity scale for such fluorinated monomers.