Synthesis and copolymerization of novel oxy ring-substituted isopropyl cyanoarylacrylates

Abstract

Novel oxy ring-substituted isopropyl 2-cyano-3-arylacrylates, RPhCH=C(CN)CO2CH(CH3)2 (where R is 3-phenoxy, 4-phenoxy, 2-benzyloxy, 3-benzyloxy, 4-benzyloxy, 4-acetyloxy, 3-acetyl, 4-acetyl, 4-acetylamino, 4-methoxy-2-methyl, 4-methoxy-3-methyl, 3-ethoxy-4-methoxy, 3,4-dibenzyloxy, 3-benzyloxy-4-methoxy, 4-benzyloxy-3-methoxy, 2,3-dimethyl-4-methoxy, 2,5-dimethyl-4-methoxy, 2,4-dimethoxy-3-methyl, 2,4-dimethoxy-6-methyl, 3,5-dimethoxy-4-hydroxy) were prepared and copolymerized with styrene. The acrylates were synthesized by the piperidine catalyzed Knoevenagel condensation of oxy ring-substituted benzaldehydes and isopropyl cyanoacetate and characterized by CHN elemental analysis, FTIR, 1H and 13C-NMR. All the acrylates were copolymerized with styrene in solution with radical initiation at 70C. The composition of the copolymers was calculated from nitrogen analysis, and the structures were analyzed by FTIR, 1H and 13C-NMR. Thermal properties of the copolymers are characterized by DSC and TGA. Decomposition of the copolymers in nitrogen occurred in two steps, first in the 200-500ºC range with a residue, which then decomposed in the 500-800ºC range.

Synthesis and styrene copolymerization of novel ring-substituted tert-butyl phenylcyanoacrylates

“…2,4, as well as its butyl PCA [18] were prepared and copolymerized with styrene, in addition to being involved in catalyst study of the Knoevenagel condensation [19]. 4-Hydroxy-3,5dimethoxyphenyl ethyl PCA is mentioned in synthesis of biologically potent heterocycles [20]; in study of main-chain and guest-host NLO polymers [21], whereas its isopropyl PCA was synthesized and copolymerized with ethenyl benzene [22].…”

Synthesis and styrene copolymerization of novel mono, di, and tri ring-substituted tert-butyl phenylcyanoacrylates

“…(2E)-3,4-Dimethoxyphenyl t-butyl PCA was involved in conjugate addition of perfluoroarenes to α,β-unsaturated carbonyls enabled by an alkoxide-hydrosilane system [7] and in preparation of acylaminobenzamide derivatives for the treatment of diseases caused by the supermultiplication of vascular intimal cells [8]. 4-Ethoxy-3-methoxyphenyl butyl [9] and isopropyl, as well as 4-hydroxy-3,5-dimethylphenyl isopropyl [10], and 4-fluoro-3methoxyphenyl isobutyl [11] PCAs were prepared and copolymerized with vinyl benzene. Synthesis and styrene copolymerization was reported for 2,3,4trimethoxyphenyl isobutyl PCA [12].…”