Synthesis and styrene copolymerization of novel dichloro and difluoro ring-substituted octyl phenylcyanoacrylates

Christian  Ibarra; Andy N.  La; Victoria  Orban; Taha  Raziuddin; Amir  Sedighzadeh; Amina  Torlo; Ania  Tyrawa; Peter A.  Wild Crea; Jessica E.  Youngs; Stephanie  Block; David C.  Dainko; Sara M.  Rocus; William S.  Schjerven; Gregory B Kharas

doi:10.26434/chemrxiv-2022-fhd7b

Organic Chemistry

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Synthesis and styrene copolymerization of novel dichloro and difluoro ring-substituted octyl phenylcyanoacrylates

Working Paper

Christian Ibarra DePaul University ,
Andy N. La DePaul University ,
Victoria Orban DePaul University ,
Taha Raziuddin DePaul University ,
Amir Sedighzadeh DePaul University ,
Amina Torlo DePaul University ,
Ania Tyrawa DePaul University ,
Peter A. Wild Crea DePaul University ,
Jessica E. Youngs DePaul University ,
Stephanie Block DePaul University ,
David C. Dainko DePaul University ,
Sara M. Rocus DePaul University ,
William S. Schjerven DePaul University ,
Gregory B Kharas DePaul University

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Abstract

Novel ring-substituted octyl phenylcyanoacrylates, RPhCH=C(CN)CO2CH2(CH2)6CH3 (where R is 2,3-dichloro, 2,4-dichloro, 2,5-dichloro, 2,6-dichloro, 3,4-dichloro, 2,3-difluoro, 2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro) were prepared and copolymerized with styrene. The acrylates were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and octyl cyanoacetate, and characterized by CHN analysis, IR, 1H and 13C NMR. All the acrylates were copolymerized with styrene in solution with radical initiation (ABCN) at 70C. The compositions of the copolymers were calculated from nitrogen analysis.