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Abstract
Novel trisubstituted ethylenes, ring-substituted propyl 2-cyano-3-phenyl-2-propenoates, RPhCH=C(CN)CO2C3H7 (where R is 2,3,6-trichloro, 2,3,4-trifluoro, 2,3,5-trifluoro, 2,4,5-trifluoro, 2,4,6-trifluoro, 3,4,5-trifluoro) were prepared by the piperidine catalyzed Knoevenagel condensation of ring-trisubstituted benzaldehydes and propyl cyanoacetate.
 
 The ethylenes when copolymerized with styrene in solution with radical initiation (ABCN) at 70°C resulted in formation of copolymers. The composition of the copolymers was calculated from nitrogen analysis. The structures and properties were characterized by IR, 1H and 13C-NMR, GPC, DSC, and TGA.
Highlights
Ring–functionalized trisubstituted ethylenes (TSE), esters of 2-cyano-3-phenyl-2-propenoic acid, R1PhCH=C(CN)CO2R2 continue to attract attention as compounds with interesting properties and as comonomers for modification of commercial polymers
Copolymerization of electrophilic TSE having double bonds substituted with halo, cyano, and carbonyl groups and electron-rich monosubstituted ethylenes such as styrene, N-vinylcarbazole, and vinyl acetate (Hall & Daly 1975, Hall & Ikman 1977, Kharas 1996) show a tendency toward the formation of alternating copolymers - suggesting a way of functionalization of commercial polymers via introduction of isolated TSE monomer units
With the objective to design novel structures, that could serve as a spring board for further development of novel materials with new properties and applications, and in continuation of our studies of the monomer structure-reactivity correlation in the radical copolymerization of TSE monomers we have prepared ring-trisubstituted propyl 2-cyano-3-phenyl-2-propenoates (PCPP), RPhCH=C(CN)CO2C3H7, where R is 2,3,6-trichloro, 2,3,4-trifluoro, 2,3,5-trifluoro, 2,4,5-trifluoro, 2,4,6-trifluoro, 3,4,5-trifluoro, and explore the feasibility of their copolymerization with styrene
Summary
Ring–functionalized trisubstituted ethylenes (TSE), esters of 2-cyano-3-phenyl-2-propenoic acid, R1PhCH=C(CN)CO2R2 continue to attract attention as compounds with interesting properties and as comonomers for modification of commercial polymers. Copolymerization of electrophilic TSE having double bonds substituted with halo, cyano, and carbonyl groups and electron-rich monosubstituted ethylenes such as styrene, N-vinylcarbazole, and vinyl acetate (Hall & Daly 1975, Hall & Ikman 1977, Kharas 1996) show a tendency toward the formation of alternating copolymers - suggesting a way of functionalization of commercial polymers via introduction of isolated TSE monomer units. With the objective to design novel structures, that could serve as a spring board for further development of novel materials with new properties and applications, and in continuation of our studies of the monomer structure-reactivity correlation in the radical copolymerization of TSE monomers we have prepared ring-trisubstituted propyl 2-cyano-3-phenyl-2-propenoates (PCPP), RPhCH=C(CN)CO2C3H7, where R is 2,3,6-trichloro, 2,3,4-trifluoro, 2,3,5-trifluoro, 2,4,5-trifluoro, 2,4,6-trifluoro, 3,4,5-trifluoro, and explore the feasibility of their copolymerization with styrene. To the best of our knowledge, there have been no reports on either synthesis of these propyl 2-cyano-3-phenyl-2-propenoates, nor their copolymerization with styrene
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