Synthesis and styrene copolymerization of novel fluoro and iodomethoxy ring-disubstituted isobutyl phenylcyanoacrylates

Abstract

<p>Novel ring-disubstituted isobutyl phenylcyanoacrylates, RPhCH=C(CN)CO<sub>2</sub>CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> (where R is 2-fluoro-3-methoxy, 2-fluoro-4-methoxy, 2-fluoro-5-methoxy, 2-fluoro-6-methoxy, 3-fluoro-4-methoxy, 4-fluoro-3-methoxy, 5-fluoro-2-methoxy, 3-iodo-4-methoxy,</p><p> 5-iodo-2-methoxy) were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-disubstituted benzaldehydes and isobutyl cyanoacetate and characterized by CHN analysis, IR, <sup>1</sup>H and <sup>13</sup>C 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. </p>

Synthesis and styrene copolymerization of novel trisubstituted ethylenes: 8. Halogen ring-disubstituted 2-methoxyethyl phenylcyanoacrylates

“…The conversion of the copolymers was kept between 10 and 20% to minimize compositional drift (Table 1). Nitrogen elemental analysis showed that between 17.2 and 28.2 mol% of MEPA is present in the copolymers prepared at ST/MEPA = 3 (mol), which is indicative of relatively high reactivity of the MEPA monomers towards ST radical which is typical of phenoxy ring-substituted phenylcyanoacrylates [18][19][20][21][22][23][24][25][26][27][28][29]. Since MEPA monomers do not homopolymerize, the most likely structure of the copolymers would be isolated MEPA monomer units alternating with short ST sequences (Scheme 2).…”