The reactivity of nitroxides towards alkenes

✍ Scribed by Fawaz Aldabbagh; W.Ken Busfield; Ian D Jenkins; San H Thang

• Book ID: 104210242
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 103 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)00440-8

✦ Synopsis

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.