The reactivity of nitroxides towards alkenes

Fawaz Aldabbagh, W. Ken Busfield, Ian D. Jenkins, San H. Thang

Research output: Contribution to journalArticleResearchpeer-review

17 Citations (Scopus)


At elevated temperatures, nitroxides (e.g. 1,1,3,3-tetramethyl-2,3- dihydroisoindol-2-yloxyl) undergo a slow addition reaction with acrylonitrile, methyl acrylate and styrene to give the bis-nitroxide adducts. With alkenes containing an allylic hydrogen such as methyl methacrylate and 6-methylene-1,4-oxathiepan-7-one, the major reaction observed was hydrogen abstraction. The resulting hydroxylamines can be trapped as Michael addition products. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)3673-3676
Number of pages4
JournalTetrahedron Letters
Issue number19
Publication statusPublished - 6 May 2000
Externally publishedYes


  • Alkene
  • Hydroxylamine
  • Nitroxide
  • Radical trapping

Cite this