Synthesis and styrene copolymerization of novel halogen and methoxy ring-disubstituted tert-butyl phenylcyanoacrylates

Abstract

Novel ring-disubstituted tert-butyl phenylcyanoacrylates, RPhCH=C(CN)CO2C(CH3)3, where R is 3-bromo-4-methoxy, 5-bromo-2-methoxy, 2-chloro-3-methoxy, 2-fluoro-4-methoxy, 2-fluoro-6-methoxy, 3-fluoro-4-methoxy, 5-fluoro-2-methoxy, 3-iodo-4-methoxy, 5-iodo-2-methoxy were prepared and copolymerized with styrene. The acrylates were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and tret-butyl cyanoacetate, and characterized by CHN analysis, IR, 1H and 13C NMR. All the acrylates were copolymerized with styrene in solution with radical initiation at 70C. The compositions of the copolymers were calculated from nitrogen analysis.