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

Abstract

<p>Novel trisubstituted ethylenes, halogen ring-disubstituted 2-methoxyethyl phenylcyanoacrylates, RPhCH=C(CN)CO<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>OCH<sub>3</sub><sub> </sub>(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, <sup>1</sup>H and <sup>13</sup>C 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.</p>

Synthesis and styrene copolymerization of novel trisubstituted ethylenes: 7. Fluoro, methyl and methoxy ring-disubstituted octyl phenylcyanoacrylates

“…Thus, copolymerization of electrophylic TSE monomers having double bonds substituted with halo, cyano, and carbonyl groups and electron-rich monosubstituted ethylenes such as styrene, N-vinylcarbazole, and vinyl acetate [16][17][18] show a tendency toward the formation of alternating copolymers -thus suggesting a way of functionalization of commercial polymers via introduction of isolated monomer units in copolymers. Earlier we have reported synthesis and styrene copolymerization of a number of fluoro, methyl and methoxy ring-disubstituted methyl [19], ethyl [20], propyl [21][22][23], isopropyl [24,25], butyl [26][27], isobutyl [28,29], and 2-methoxyethyl [30] PCAs.…”