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Synthesis and Styrene Copolymerization of New Halogen and Methoxy Ring-Trisubstituted Propyl Cyanophenylpropenoates

Author

Listed:
  • Yesenia L. Soto
  • Emily A. Baumgartner
  • Francesca R. Bertoletti
  • Ellen F. Gardner
  • Bridget M. Hofsteadter
  • Adis Hrvat
  • Aurimas Jackunas
  • Alex J. Jagla
  • Justus V. Winter
  • Danielle S. Ostrovsky
  • William S. Schjerven
  • Gregory B. Kharas

Abstract

New ring-trisubstituted propyl cyanophenylpropenoates, RPhCH=C(CN)CO2C3H7 (where R is 2-bromo-3-hydroxy-4-methoxy, 5-bromo-2,3-dimethoxy, 5-bromo-2,4-dimethoxy, 6-bromo-3,4-dimethoxy, 2-chloro-3,4-dimetoxy, 5-chloro-2,3-dimetoxy, 4-bromo-2,6-difluoro, 3-chloro-2,6-difluoro, 4-chloro-2,6-difluoro) were prepared by the piperidine catalyzed Knoevenagel condensation of ring-trisubstituted benzaldehydes and propyl cyanoacetate and characterized by CHN elemental analysis, IR, 1H and 13C-NMR. The propenoates formed copolymers with styrene in solution with radical initiation (ABCN) at 70C. The copolymers were characterized by nitrogen elemental analysis, IR, 1H and 13C-NMR, DSC. Decomposition of the copolymers in nitrogen (TGA) occurred in two steps, first in the 200-500oC range with residue (4.2 -8.1% wt.), which then decomposed in the 500-800oC range.

Suggested Citation

  • Yesenia L. Soto & Emily A. Baumgartner & Francesca R. Bertoletti & Ellen F. Gardner & Bridget M. Hofsteadter & Adis Hrvat & Aurimas Jackunas & Alex J. Jagla & Justus V. Winter & Danielle S. Ostrovsky , 2019. "Synthesis and Styrene Copolymerization of New Halogen and Methoxy Ring-Trisubstituted Propyl Cyanophenylpropenoates," International Journal of Chemistry, Canadian Center of Science and Education, vol. 11(2), pages 60-66, November.
    • Handle: RePEc:ibn:ijcjnl:v:11:y:2019:i:2:p:60-66
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