Mechanistic investigation of the isomerization of 5-vinyl-2-norbornene

Hoon Sik Kim; So Young Lee; Hyunjoo Lee; Jin Young Bae; Sang Joon Park; Minserk Cheong; Je Seung Lee; Chang Ha Lee

doi:10.1021/jo0518203

Mechanistic investigation of the isomerization of 5-vinyl-2-norbornene

Hoon Sik Kim, So Young Lee, Hyunjoo Lee, Jin Young Bae, Sang Joon Park, Minserk Cheong, Je Seung Lee, Chang Ha Lee

Department of Chemical and Biomolecular Engineering

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

7 Citations (Scopus)

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	https://doi.org/10.1021/jo0518203
Publication status	Published - 2006 Feb 3

All Science Journal Classification (ASJC) codes

Organic Chemistry

Access to Document

10.1021/jo0518203

Cite this

@article{0af59cc0d5fd41ffac52a6486ddeebfd,

title = "Mechanistic investigation of the isomerization of 5-vinyl-2-norbornene",

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.",

author = "Kim, {Hoon Sik} and Lee, {So Young} and Hyunjoo Lee and Bae, {Jin Young} and Park, {Sang Joon} and Minserk Cheong and Lee, {Je Seung} and Lee, {Chang Ha}",

year = "2006",

month = feb,

day = "3",

doi = "10.1021/jo0518203",

language = "English",

volume = "71",

pages = "911--914",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "3",

}

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.

UR - http://www.scopus.com/inward/record.url?scp=32144455691&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=32144455691&partnerID=8YFLogxK

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 -

Mechanistic investigation of the isomerization of 5-vinyl-2-norbornene

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this