Synthesis and styrene copolymerization of novel dibromo and dichloro ring-disubstituted isobutyl phenylcyanoacrylates

Daniah H. Ibrahim; Chris J. Lee; Daniel N. Madock; Marcin Marciniak; Miguel A. Montero; Juan Orozco; Viany Ortiz; Mica C. Robles; Sara M. Rocus; William S. Schjerven; Gregory Kharas

doi:10.26434/chemrxiv.11401347.v8

Organic Chemistry

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Synthesis and styrene copolymerization of novel dibromo and dichloro ring-disubstituted isobutyl phenylcyanoacrylates

25 September 2020, Version 8

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Abstract

Novel ring-disubstituted isobutyl phenylcyanoacrylates, RPhCH=C(CN)CO₂CH₂CH(CH₃)₂ (where R is 2,5-dibromo, 3,5-dibromo, 2,3-dichloro, 2,4-dichloro, 2,5-dichloro, 2,6-dichloro, 3,4-dichloro, 3,5-dichloro) were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-disubstituted benzaldehydes and isobutyl cyanoacetate and characterized by CHN analysis, IR, ¹H and ¹³C 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.

Keywords

phenyl cyanoacrylates

radical copolymerization

styrene copolymers

Knoevenagel condensation products

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