H. K. Hall, Y. Okamoto
Jul 1, 1974
Citations
0
Influential Citations
2
Citations
Journal
Journal of Polymer Science Part A
Abstract
3,3-Difluorocyclobutene-1-carbonitrile (DFCB) was synthesized via cycloaddition of 1-chloro-2,2-difluoroethylene and acrylonitrile, followed by dehydrochlorination with 1,4-diazabicyclo[2.2.2]octane in tetrahydrofuran. Unlike cyclobutene-1-carbonitrile, this monomer did not homopolymerize either under radical or anionic conditions. As an electron-poor monomer it copolymerized in the presence of free radicals with electronrich monomers such as styrene in good yield. It also copolymerized with electron-poor monomers such as acrylonitrile, although in lower yields. The extent of incorporation of DFCB in the copolymers also depended on the electronic characteristics of the comonomers: high incorporation occurred with electron-rich monomers, low incorporation with electron-poor monomers. One extremely electron-poor monomer, trimethyl ethylenetricarboxylate, did not copolymerize with DFCB.