Macromolecular Rapid Communications, Vol.24, No.3, 269-273, 2003
Polymerization of cyclic monomers, 10 - Synthesis and radical polymerization of methyl 2-(bicyclo[3.1.0]hex-1-yl)acrylate
Methyl 2-(bicyclo[3.1.0]hex-1-yl)acrylate (1) was synthesized from methyl 2-(cyclopentene-1-yl)-2-hydroxyacetate by cyclopropanation, followed by oxidation to the corresponding bicyclic 2-oxoacetate and Wittig olefination with methyltriphenylphosphonium bromide. Initiated with 2,2'-azoisobutyronitrile at 65 degreesC in chlorobenzene, the radical homopolymerization of 1 occurred with a glass transition temperature of 90 degreesC. The reactivity of 1 in radical copolymerization was higher than that of methyl methacrylate.
Keywords:dental polymers;polymerization shrinkage;radical polymerization;ring-opening polymerization;vinylcyclopropanes