ChemInform Abstract: ISOMERIZATION OF 5‐VINYL‐2‐NORBORNENE INTO 5‐ETHYLIDENE‐2‐NORBORNENE IN THE PRESENCE OF IRON CARBONYLS

Osokin, Yu. G.; Grinberg, M. Ya.; Fel'dblyum, V. Sh.; Tseitlin, I. L.; Belikova, N. A.; Platé, A. F.

doi:10.1002/chin.198042078

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2005

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“…[5][6][7] There are also known liquid bases, for example, mixtures of an alkali metal hydroxide and an aprotic organic solvent and of an alkali metal amide and an amine. Organometallic complexes including Ti, 4,8 Co, 9,10 and Fe 11 are other types of catalysts used for the isomerization. The industrial application of these liquid bases and organometallic complexes, however, has been restricted because of their low catalytic activities.…”

Section: Introductionmentioning

confidence: 99%

Mechanistic Investigation of the Isomerization of 5-Vinyl-2-norbornene

Kim

Lee

et al. 2005

J. Org. Chem.

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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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