Synthesis and styrene copolymerization of novel trisubstituted ethylenes: 5. Halogen ring-substituted 2-methoxyethyl phenylcyanoacrylates

Novel trisubstituted ethylenes, ring-substituted 2-methoxyethyl phenylcyanoacrylates, RPhCH=C(CN)CO₂CH₂CH₂OCH₃ (where R is 2-bromo, 3-bromo, 4-bromo, 2-chloro, 3-chloro, 4-chloro, 2-fluoro, 3-fluoro, 4-fluoro, 2-trifluoromethyl, 3-trifluoromethyl, 4-trifluoromethyl) were prepared and copolymerized with styrene. The ethylenes were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and 2-methoxyethyl cyanoacetate, and characterized by CHN analysis, IR, ¹H and ¹³C NMR. All the ethylenes were copolymerized with styrene in solution with radical initiation (ABCN) at 70°C. The compositions of the copolymers were calculated from nitrogen analysis.