Abstract
Nitroxides bearing an α-hydrogen decompose upon heating in a bimolecular reaction. A new mechanism is proposed for the decomposition of t-butylisopropyl-phenyl nitroxide (TIPNO) involving the formation of a head-to-tail dimer, single electron transfer to form an oxammonium salt, epimerization to the corresponding nitrone, and elimination to form a conjugated oxime. This mechanism may provide insights into designing new nitroxides for use in controlled polymerization.
Original language | English (US) |
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Pages (from-to) | 697-717 |
Number of pages | 21 |
Journal | Journal of Polymer Science, Part A: Polymer Chemistry |
Volume | 44 |
Issue number | 2 |
DOIs | |
State | Published - Jan 15 2006 |
Externally published | Yes |
Keywords
- Decomposition
- Electron transfer
- Initiators
- Living polymerization
- Nitroxide
- Radical polymerization
ASJC Scopus subject areas
- Polymers and Plastics
- Organic Chemistry
- Materials Chemistry