Asymmetric cyclopolymerization of N-tert-butyl-N-allylacrylamide in the presence of β-cyclodextrin

✍ Scribed by Makiko Seno; Toshiya Ikezumi; Takafumi Sumie; Yasuhito Masuda; Tsuneyuki Sato

• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: English
• Weight: 162 KB
• Volume: 38
• Category: Article
• ISSN: 0887-624X
• DOI: 10.1002/(sici)1099-0518(20000601)38:11<2098::aid-pola190>3.0.co;2-o

✦ Synopsis

The radical polymerization of N-tert-butyl-N-allylacrylamide (t-BAA) was carried out in a dimethyl sulfoxide/H 2 O mixture in the presence of ␤-cyclodextrin (␤-CD). The polymerization proceeded with the complete cyclization of the t-BAA unit and yielded optically active poly(t-BAA). The IR spectrum of the obtained polymer showed that the cyclic structure in the polymer was a five-membered ring. The optical activity of poly(t-BAA) increased with an increasing molar ratio of ␤-CD to the t-BAA monomer. The interaction of ␤-CD with t-BAA was confirmed by 1 H NMR and 13 C NMR analyses of the polymerization system. It is suggested that interaction of the t-BAA monomer with the hydrophobic cavity of ␤-CD plays an important role in the asymmetric cyclopolymerization of t-BAA. The radical copolymerization of t-BAA with styrene (St), methyl methacrylate, ethyl methacrylate, or benzyl methacrylate (BMA) also produced optically active copolymers with a cyclic structure from the t-BAA unit. St and BMA carrying a phenyl group were predicted to compete with t-BAA for interaction with ␤-CD in the copolymerization system.