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Synthesis and Styrene Copolymerization of Novel Ring-Disubstituted Isopropyl Cyanoarylacrylates

preprint
submitted on 23.09.2019, 03:37 and posted on 24.09.2019, 22:34 by Paige M. Whelpley, Sejla Bajramovic, Destiny M. Bracamontes, Garrett A. Buechner, Alexander D. Eremin, Erik J. Kowalczyk, David D. Lender, Rachel McCann, William S. Schjerven, Gregory Kharas

Novel oxy ring-substituted isopropyl 2-cyano-3-arylacrylates, RPhCH=C(CN)CO2CH(CH3)2 (where R is 3,4-dibenzyloxy, 3-benzyloxy-4-methoxy, 4-benzyloxy-3-methoxy, 2,3-methylenedioxy, 3-iodo-4-methoxy, 5-iodo-2-methoxy, 3,4-difluoro, 3,5-difluoro) were prepared and copolymerized with styrene. The acrylates were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-disubstituted benzaldehydes and isopropyl cyanoacetate and characterized by CHN elemental analysis, FTIR, 1H and 13C-NMR. All the acrylates were copolymerized with styrene in solution with radical initiation (ABCN) at 70°C. The composition of the copolymers was calculated from nitrogen analysis, and the structures were analyzed by FTIR, 1H and 13C-NMR. Thermal properties of the copolymers are characterized by DSC and TGA. Decomposition of the copolymers in nitrogen occurred in two steps, first in the 200-500ºC range with a residue, which then decomposed in the 500-800ºC range.

History

Email Address of Submitting Author

gkharas@depaul.edu

Institution

DePaul University

Country

USA

ORCID For Submitting Author

0000-0003-3778-7970

Declaration of Conflict of Interest

No conflict of interest

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