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 comonom ers 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 t he best initiator. Then, the selective reduction of the iodine atom in the presence of tributyl stannane gave CICF2CFCIC3H6OH quantitatively and its d echlorination was optimized leading to F2C=CFC3H6OH in 50% overall yield fr om (1). This monomer was quantitatively acetylated by acetyl chloride. All these products and intermediates were characterized by H-1 F-19 and C-13-NM R spectroscopy, and simulated spectra were in very good agreement with thos e observed experimentally. (C) 1998 Elsevier Science S.A. All rights reserv ed.