Abstract
This chapter describes a new stereoregulation method for free-radical polymerization of vinyl esters using fluoroalcohols as solvents. The stereochemistry of the vinyl ester polymerization was remarkably affected by the fluoroalcohols such as (CF3)3COH and (CF3)2CHOH. The polymerization of vinyl acetate (VAc) gave a polymer rich in syndiotacticity (up to rr = 50%, r = 72%), while the polymerization of vinyl propionate (VPr), vinyl isobutyrate (ViBu), vinyl pivalate ( VPi), vinyl 2,2-dimethylbutylate (VDMB), and vinyl 2,2-dimethylvalerate (VDMV) gave polymers rich in heterotacticity (up to mr = 61%). A polymer rich in isotacticity (up to mm = 33%) was obtained by the polymerization of vinyl benzoate (VBz). This stereochemistry represents the highest level of content for the radical polymerization of vinyl esters reported so far. The stereochemical effects observed in this study are due to a hydrogen-bonding interaction between the fluoroalcohol molecules and the ester groups of the vinyl ester monomer and the growing polymer. Conversely, the stereochemistry of the polymerization of bulky 2,2-bis(trifluoromethyl)propionate (VF6Pi) in fluoroalcohols was similar to that of the bulk polymerization presumably due to the weak hydrogen-bonding interaction between the monomer and the fluoroalcohols.
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