Abstract
The isomerization reaction of 5-vinyl-2-norbornene (VNB) to 5-ethylidene-2-norbornene (ENB) has been performed using a catalytic system consisting of an alkali metal hydride and an amine. Among various amines tested, only aliphatic 1,2-diamines exhibited the activity for the isomerization. The isomerization was also affected by the alkali metal hydride employed. The activity of the alkali metal hydride increased with the increasing size of alkali metal: KH > NaH > LiH. A series of electron paramagnetic resonance (EPR) and UV-vis experiments on the active species suggest that the isomerization of VNB proceeds through a radical mechanism.
| Original language | English |
|---|---|
| Pages (from-to) | 911-914 |
| Number of pages | 4 |
| Journal | Journal of Organic Chemistry |
| Volume | 71 |
| Issue number | 3 |
| DOIs | |
| Publication status | Published - 2006 Feb 3 |
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All Science Journal Classification (ASJC) codes
- Organic Chemistry
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Mechanistic investigation of the isomerization of 5-vinyl-2-norbornene. / Kim, Hoon Sik; Lee, So Young; Lee, Hyunjoo; Bae, Jin Young; Park, Sang Joon; Cheong, Minserk; Lee, Je Seung; Lee, Chang-Ha.
In: Journal of Organic Chemistry, Vol. 71, No. 3, 03.02.2006, p. 911-914.Research output: Contribution to journal › Article
TY - JOUR
T1 - Mechanistic investigation of the isomerization of 5-vinyl-2-norbornene
AU - Kim, Hoon Sik
AU - Lee, So Young
AU - Lee, Hyunjoo
AU - Bae, Jin Young
AU - Park, Sang Joon
AU - Cheong, Minserk
AU - Lee, Je Seung
AU - Lee, Chang-Ha
PY - 2006/2/3
Y1 - 2006/2/3
N2 - The isomerization reaction of 5-vinyl-2-norbornene (VNB) to 5-ethylidene-2-norbornene (ENB) has been performed using a catalytic system consisting of an alkali metal hydride and an amine. Among various amines tested, only aliphatic 1,2-diamines exhibited the activity for the isomerization. The isomerization was also affected by the alkali metal hydride employed. The activity of the alkali metal hydride increased with the increasing size of alkali metal: KH > NaH > LiH. A series of electron paramagnetic resonance (EPR) and UV-vis experiments on the active species suggest that the isomerization of VNB proceeds through a radical mechanism.
AB - The isomerization reaction of 5-vinyl-2-norbornene (VNB) to 5-ethylidene-2-norbornene (ENB) has been performed using a catalytic system consisting of an alkali metal hydride and an amine. Among various amines tested, only aliphatic 1,2-diamines exhibited the activity for the isomerization. The isomerization was also affected by the alkali metal hydride employed. The activity of the alkali metal hydride increased with the increasing size of alkali metal: KH > NaH > LiH. A series of electron paramagnetic resonance (EPR) and UV-vis experiments on the active species suggest that the isomerization of VNB proceeds through a radical mechanism.
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U2 - 10.1021/jo0518203
DO - 10.1021/jo0518203
M3 - Article
C2 - 16438500
AN - SCOPUS:32144455691
VL - 71
SP - 911
EP - 914
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 3
ER -