Synthesis and vinyl benzene copolymerization of novel trisubstituted ethylenes: 15. Halogen and methoxy ring-substituted isopropyl 2-cyano-3-phenyl-2-propenoates

Abstract

Condensation of isopropyl cyanoacetate and substituted benzoic aldehydes resulted in formation of novel isopropyl esters of 2-cyano-3-phenyl-2-propenoic acid, RPhCH = C(CN)CO2CH(CH3)2 (where R is 2,3,4-trimethoxy, 2,4,5-trimethoxy, 2,4,6-trimethoxy, 3-bromo-4,5-dimethoxy, 5-bromo-2,3-dimethoxy, 5-bromo-2,4-dimethoxy, 6-bromo-3,4-dimethoxy, 2-bromo-3-hydroxy-4-methoxy, 4-bromo-2,6-difluoro, 2-chloro-3,4-dimethoxy, 3-chloro-4,5-dimethoxy, 5-chloro-2,3-dimethoxy, 2,3,6-trichloro, 3-chloro-2,6-difluoro, 2,3,4-trifluoro, 2,4,5-trifluoro, 2,4,6-trifluoro, 3,4,5-trifluoro, 2,3,5,6-tetrafluoro, 2,3,4,5,6-pentafluoro). Copolymerization of the esters with vinyl benzene in solution with radical initiation (ABCN) at 70°C led to formation copolymers. The products were characterized by CHN elemental analysis, IR, 1 H- and 13 C-NMR, GPC, DSC, and TGA.

Keywords

• isopropyl cyanopropenoates
• knoevenagel condensation
• radical copolymerization
• vinyl benzene copolymers