A New Acyclic α-Hydrogen Bearing Nitroxide and its Corresponding Alkoxyamine for Stable Free Radical Polymerization
✍ Scribed by Silke Flakus; Kerstin Mandel; Martina Bartsch; Gudrun Schmidt-Naake
- Publisher
- John Wiley and Sons
- Year
- 2005
- Tongue
- English
- Weight
- 123 KB
- Volume
- 26
- Category
- Article
- ISSN
- 1022-1336
No coin nor oath required. For personal study only.
✦ Synopsis
Abstract
Summary: The synthesis of the new α‐hydrogen bearing nitroxide, 2,2,5‐trimethyl‐4‐(isopropyl)‐3‐azahexane‐3‐oxyl (BIPNO) (4), and its corresponding alkoxyamine, N‐tert‐butyl‐N‐(1‐isopropyl‐2‐methyl‐propyl)‐O‐(1‐phenyl‐ethyl)‐hydroxylamine (PhEt‐BIPNO) (7), are described in this paper. Reaction of styrene with the new nitroxide in the presence of a Jacobsen‐like manganese catalyst, Mn(salen)Cl, at ambient atmosphere afforded the alkoxyamine in 96% yield. Styrene and n‐butyl acrylate were polymerized in bulk in the presence of the new alkoxyamine. The alkoxyamine turned out to be a suitable “initiator” for controlled radical polymerization.
Structure of α‐hydrogen bearing nitroxide and its corresponding alkoxyamine.
magnified imageStructure of α‐hydrogen bearing nitroxide and its corresponding alkoxyamine.