Lipase-catalyzed polymerization of fluorinated lactones and fluorinated hydroxycarboxylic acids

✍ Scribed by Martina Runge; David O'Hagan; Günter Haufe

• Book ID: 101278168
• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: English
• Weight: 160 KB
• Volume: 38
• Category: Article
• ISSN: 0887-624X
• DOI: 10.1002/(sici)1099-0518(20000601)38:11<2004::aid-pola90>3.0.co;2-t

✦ Synopsis

Lipase-catalyzed ring-opening polymerization of 10-fluorodecan-9-olide (1a), 11-fluoroundecan-10-olide (1b), 12-fluorododecan-11-olide (1c) and 14-fluorotetradecan-13-olide (1d) gave optically active products with M w of 3.000 to 8.000, while 10-fluoroundecan-11-olide (3a) gave an optically inactive polymer with M w ϭ 11.000. On the other hand, Candida antarctica lipase-catalyzed polymerization of 10-to 14membered -fluoro-(-1)-hydroxyalcanoic acids gave optically inactive oligomers with M w of 3.000 to 11.000 in the presence of molecular sieves, while reactions without molecular sieves gave oligomers with lower molecular weight, but with small optical rotations. 9-Fluoro-10-hydroxydecanoic acid, on the other hand, gave an optically inactive polyester with M w ϭ 7400.