The reactivity of nitroxides towards alkenes

Authors
Aldabbagh, F Busfield, WK Jenkins, ID Thang, SH
Citation
F. Aldabbagh et al., The reactivity of nitroxides towards alkenes, TETRAHEDR L, 41(19), 2000, pp. 3673-3676
Citations number
11
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
19
Year of publication
2000
Pages
3673 - 3676
Database
ISI
SICI code
0040-4039(20000506)41:19<3673:TRONTA>2.0.ZU;2-M
Abstract
At elevated temperatures, nitroxides (e.g. 1,1,3,3-tetramethyl-2,3-dihydroi soindol-2-yloxyl) undergo a slow addition reaction with acrylonitrile, meth yl acrylate and styrene to give the bis-nitroxide adducts. With alkenes con taining an allylic hydrogen such as methyl methacrylate and 6-methylene-1,4 -oxathiepan-7-one, the major reaction observed was hydrogen abstraction. Th e resulting hydroxylamines can be trapped as Michael addition products. (C) 2000 Elsevier Science Ltd. All rights reserved.