Synthesis and styrene copolymerization of novel trisubstituted ethylenes: 11. Halogen ring-substituted propyl 2-cyano-3-phenyl-2-propenoates

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

“…Our purposes in exploration of novel propyl cyanophenylpropenoates were twofold: (1) to utilize aldol condensation for synthesis of alkenes with a variety of potentially reactive functional groups; (2) to employ conventional radical copolymerization of novel functional comonomers with a commercial monomer styrene. Thus, in continuation of our investigation of new of propyl cyanophenylpropenoates (Bates et al, 2019, Humanski et al, 2018, Kharas et al, 2017 we have prepared halogen and methoxy ring-trisubstituted propyl cyanophenylpropenoates (PCPP), RPhCH=C(CN)CO 2 C 3 H 7 , 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, and explore the feasibility of their copolymerization with styrene. To the best of our knowledge, there have been no reports on either synthesis of these propyl cyanophenylpropenoates, nor their copolymerization with styrene.…”

Synthesis and styrene copolymerization of novel difluoro and chlorofluoro ring-disubstituted isobutyl phenylcyanoacrylates

“…The conversion of the copolymers was kept between 10 and 20% to minimize compositional drift (Table 1). Nitrogen elemental analysis showed that between 14.7 and 34.2 mol% of IPCA is present in the copolymers, which is indicative of relatively high reactivity of the IPCA monomers towards ST radical which is typical of halogen ring-substituted different esters PCA [17][18][19][20][21][22][23][24][25][26][27][28][29]. Since IPCA monomers do not homopolymerize, the most likely structure of the copolymers would be isolated IPCA monomer (y = 1) units alternating with short ST sequences (x > 1) (Scheme 2).…”

“…Earlier we have reported synthesis and styrene copolymerization a number of difluoro and chlorofluoro ring-disubstituted PCAs, such esters as methyl [17][18][19], ethyl [20], propyl [21][22][23], isopropyl [24][25][26], and butyl [27,28].…”