Synthesis and polymerization of fluorinated monomers bearing a reactive lateral group.: Part 3 -: Synthesis of trifluorovinyl hydroxy and acetoxy monomers

The preparation of two functional perfluorovinyl monomers useful as comonomers in the copolymerization of commercially available monomers is presented. First, 1-iodo-1,2-dichloro-1,2,2-trifluoro ethane (1) was added to allyl alcohol under several initiating conditions and it was found that AIBN is the best initiator. Then, the selective reduction of the iodine atom in the presence of tributyl stannane gave CICF2CFCIC3H6OH quantitatively and its dechlorination was optimized leading to F2C=CFC3H6OH in 50% overall yield from (1). This monomer was quantitatively acetylated by acetyl chloride. All these products and intermediates were characterized by H-1 F-19 and C-13-NMR spectroscopy, and simulated spectra were in very good agreement with those observed experimentally. (C) 1998 Elsevier Science S.A. All rights reserved.