Nitroxide decomposition: Implications toward nitroxide design for applications in living free-radical polymerization

Aaron Nilsen, Rebecca Braslau

Research output: Contribution to journalArticle

76 Scopus citations

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 languageEnglish (US)
Pages (from-to)697-717
Number of pages21
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume44
Issue number2
DOIs
StatePublished - Jan 15 2006

Keywords

  • Decomposition
  • Electron transfer
  • Initiators
  • Living polymerization
  • Nitroxide
  • Radical polymerization

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

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