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

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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 languageEnglish
Pages (from-to)911-914
Number of pages4
JournalJournal of Organic Chemistry
Volume71
Issue number3
DOIs
Publication statusPublished - 2006 Feb 3

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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    Kim, H. S., Lee, S. Y., Lee, H., Bae, J. Y., Park, S. J., Cheong, M., Lee, J. S., & Lee, C. H. (2006). Mechanistic investigation of the isomerization of 5-vinyl-2-norbornene. Journal of Organic Chemistry, 71(3), 911-914. https://doi.org/10.1021/jo0518203