Synthesis and copolymerization of 2-cyano-1-oxo-3-halophenyl–2-propenyl ethyl urethanes with styrene

CHED 813

S. Behbahani, A. Lorenz, N. Fliman, A. Reznick, V. Salcedo, B. Shepherd, S. Skucha, T. Taylor, N. Du, C. Dittmann, S. Morris, J. Drandakis, and GB. Kharas. DePaul University, Chicago, IL 60614
New trisubstituted ethylenes, 2-cyano-1-oxo-3-halophenyl–2-propenyl ethyl urethanes were prepared as a part of an inquiry-based, sophomore organic laboratory course. The compounds were synthesized by the piperidine catalyzed Knoevenagel condensation of an appropriate substituted benzaldehyde and N-cyanoacetylurethane. The compounds were characterized by CHN elemental analysis, mp, IR and NMR spectroscopy. Feasibility studies of the copolymerizability of the trisubstituted ethylenes with styrene were conducted in solution in the presence of a radical initiator, ABCN. The composition, structure, and some properties of the copolymers were characterized by elemental analysis, IR, NMR, GPC and thermal analysis.