The reactivity of nitroxides towards alkenes

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

doi:10.1016/S0040-4039(00)00440-8

The reactivity of nitroxides towards alkenes

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

Research output: Contribution to journal › Article › Research › peer-review

24 Citations (Scopus)

Abstract

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 language	English
Pages (from-to)	3673-3676
Number of pages	4
Journal	Tetrahedron Letters
Volume	41
Issue number	19
DOIs	https://doi.org/10.1016/S0040-4039(00)00440-8
Publication status	Published - 6 May 2000
Externally published	Yes

Keywords

Alkene
Hydroxylamine
Nitroxide
Radical trapping

Access to Document

10.1016/S0040-4039(00)00440-8

Link to publication in Scopus

Cite this

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title = "The reactivity of nitroxides towards alkenes",

abstract = "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.",

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author = "Fawaz Aldabbagh and Busfield, {W. Ken} and Jenkins, {Ian D.} and Thang, {San H.}",

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T1 - The reactivity of nitroxides towards alkenes

AU - Aldabbagh, Fawaz

AU - Busfield, W. Ken

AU - Jenkins, Ian D.

AU - Thang, San H.

PY - 2000/5/6

Y1 - 2000/5/6

N2 - 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.

AB - 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.

KW - Alkene

KW - Hydroxylamine

KW - Nitroxide

KW - Radical trapping

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U2 - 10.1016/S0040-4039(00)00440-8

DO - 10.1016/S0040-4039(00)00440-8

M3 - Article

AN - SCOPUS:0034612051

VL - 41

SP - 3673

EP - 3676

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 19

ER -