Stereospecific radical polymerization of optically active (S)-N-(2-hydroxy-1-phenylethyl) methacrylamide catalyzed by Lewis acids

作者：Xu, Xiaodong^*; Feng, Siwei; Zhu, Yuanqi; Li, Han; Shen, Xiande; Zhang, Chunhong; Bai, Jianwei; Zhang, Lili

来源：European Polymer Journal, 2013, 49(11): 3673-3680.

DOI：10.1016/j.eurpolymj.2013.07.035

• Stereospecific polymerization
• Optically active polymer
• Polymethacrylamide
• Lewis acid
• Tacticity

The effects of Lewis acids, namely, rare earth metal trifluoromethanesulfonates, on the radical polymerization of (S)-N-(2-hydroxy-1-phenylethyl) methacrylamide were examined under various conditions. In the absence of Lewis acids, syndiotactic-rich polymers (r = 84%) were obtained, whereas in the presence of a catalytic amount of Lewis acids, the polymerization proceeded in an isotactic-speciflc manner (us up to 64%). Polymerization solvents strongly influenced the effect of the Lewis acids. The polymerization in n-butyl alcohol showed the highest isotactic selectivity, whereas the polymerization in DMSO showed no isotacticity-enhancing effect. Further increases in the Lewis acid concentration and the polymerization temperature did not produce clear effects on the tacticity of the polymers. The interaction between the monomer and Lewis acids was investigated, and the plausible mechanism of stereocontrol in the radical polymerization of (S)-HPEMA was analyzed based on the Lewis acid-monomer interaction.

• 出版日期2013-11
• 单位哈尔滨工程大学