Synthesis and styrene copolymerization of novel ring-disubstituted isobutyl phenylcyanoacrylates

Abstract

<p>Novel oxy ring-disubstituted isobutyl phenylcyanoacrylates, RPhCH=C(CN)CO<sub>2</sub>CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> (where R is 2-bromo-3-methoxy, 2-bromo-5-methoxy, 3-bromo-4-methoxy, 5-bromo-2-methoxy, 2-bromo-4-methyl, 2-chloro-3-methoxy, 3-chloro-4-methoxy, 3-chloro-4-methyl) were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-disubstituted benzaldehydes and isobutyl cyanoacetate and characterized by CHN analysis, IR, <sup>1</sup>H and <sup>13</sup>C NMR. The acrylates were copolymerized with styrene in solution with radical initiation (ABCN) at 70C. The compositions of the copolymers were calculated from nitrogen analysis. <br></p>

Synthesis and styrene copolymerization of novel bromo, chloro, methoxy, and methyl ring-disubstituted isobutyl phenylcyanoacrylates

“…Chloro and methyl isopropyl PCA was used in tunable Cinchona-Based thioureas-catalysed asymmetric epoxidation to synthetically important glycidic ester derivatives [15]. Earlier we have reported synthesis and styrene copolymerization a number of bromo, chloro, methoxy, and methyl ring-disubstituted PCAs, as methyl [16], ethyl [17], propyl [18,19], isopropyl [20], butyl [21], isobutyl [22], methoxyethyl [23], and octyl [24].…”

Synthesis and styrene copolymerization of novel trisubstituted ethylenes: 6. Methyl, halogen and oxy 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 methyl, halogen, and oxy ring-disubstituted methyl [19][20][21], ethyl [22][23][24], propyl [25][26][27], isopropyl [28][29][30], butyl [31,32], isobutyl [33,34], and 2-methoxyethyl [35] PCAs.…”

Synthesis and styrene copolymerization of novel trisubstituted ethylenes: 6. Methyl, halogen and oxy 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 methyl, halogen, and oxy ring-disubstituted methyl [19][20][21], ethyl [22][23][24], propyl [25][26][27], isopropyl [28][29][30], butyl [31,32], isobutyl [33,34], and 2-methoxyethyl [35] PCAs.…”