Synthesis and styrene copolymerization of novel trisubstituted ethylenes: 8. Halogen ring-disubstituted 2-methoxyethyl phenylcyanoacrylates

Novel trisubstituted ethylenes, halogen ring-disubstituted 2-methoxyethyl phenylcyanoacrylates, RPhCH=C(CN)CO₂CH₂CH₂OCH₃ (where R is 2-fluoro-3-methoxy, 2-fluoro-4-methoxy, 2-fluoro-5-methoxy, 2-fluoro-6-methoxy, 3-fluoro-4-methoxy, 4-fluoro-3-methoxy, 2-fluoro-5-methyl, 2-fluoro-6-methyl, 3-fluoro-4-methyl, 4-fluoro-2-methyl, 4-fluoro-3-methyl, 4-fluoro-3-phenoxy, 5-iodo-2-methoxy) 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.