Vinyl norbornene

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Vinyl norbornene
VNB.svg
Names
IUPAC name
5-Ethenylbicyclo[2.2.1]hept-2-ene
Other names
2-Ethylidene-5-norbornene; 5-Vinyl-2-norbornene
Identifiers
3D model (JSmol)
PubChem CID
UNII
  • InChI=1S/C9H12/c1-2-8-5-7-3-4-9(8)6-7/h2-4,7-9H,1,5-6H2
    Key: INYHZQLKOKTDAI-UHFFFAOYSA-N
  • C=CC1CC2CC1C=C2
Properties
C9H12
Molar mass 120.195 g·mol−1
AppearanceColorless liquid
Boiling point 141 °C (286 °F; 414 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Vinyl norbornene (VNB) is an organic compound that consists of a vinyl group attached to norbornene. It is a colorless liquid. The compound exists as endo and exo isomers, but these are not typically separated. It is an intermediate in the production of the commercial polymer EPDM. It is prepared by the Diels-Alder reaction of butadiene and cyclopentadiene. [1]

Vinyl norbornene is an intermediate in the production ethylidene norbornene. RouteToEthylidenenorbornene.svg
Vinyl norbornene is an intermediate in the production ethylidene norbornene.

Safety

LD50 (intravenous, rabbit = 0.10–0.05 mg/kg(female). It is also a neurotoxin. [2]

Related Research Articles

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<span class="mw-page-title-main">Alkyne</span> Hydrocarbon compound containing one or more C≡C bonds

In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and no other functional groups form a homologous series with the general chemical formula CnH2n−2. Alkynes are traditionally known as acetylenes, although the name acetylene also refers specifically to C2H2, known formally as ethyne using IUPAC nomenclature. Like other hydrocarbons, alkynes are generally hydrophobic.

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<span class="mw-page-title-main">Bredt's rule</span>

In organic chemistry, Bredt's rule is an empirical observation that states that a double bond cannot be placed at the bridgehead of a bridged ring system, unless the rings are large enough. The rule is named after Julius Bredt, who first discussed it in 1902 and codified it in 1924. It primarily relates to bridgeheads with carbon-carbon and carbon-nitrogen double bonds.

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<span class="mw-page-title-main">Methyl vinyl ketone</span> Chemical compound

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<span class="mw-page-title-main">Dewar benzene</span> Chemical compound

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<span class="mw-page-title-main">Dichlorotetrakis(dimethylsulfoxide)ruthenium(II)</span> Chemical compound

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<span class="mw-page-title-main">Ethylidene norbornene</span> Chemical compound

Ethylidene norbornene (ENB) is an organic compound that consists of an ethylidene (CH3C(H)=) group attached to norbornene. It is a colorless liquid. The molecule consists of two sites of unsaturation. The compound consists of E- and Z-stereoisomers, but the mixtures are typically not separated.

<span class="mw-page-title-main">Mizoroki-Heck vs. Reductive Heck</span>

The Mizoroki−Heck coupling of aryl halides and alkenes to form C(sp2)–C(sp2) bonds has become a staple transformation in organic synthesis, owing to its broad functional group compatibility and varied scope. In stark contrast, the palladium-catalyzed reductive Heck reaction has received considerably less attention, despite the fact that early reports of this reaction date back almost half a century. From the perspective of retrosynthetic logic, this transformation is highly enabling because it can forge alkyl–aryl linkages from widely available alkenes, rather than from the less accessible and/or more expensive alkyl halide or organometallic C(sp3) synthons that are needed in a classical aryl/alkyl cross-coupling.

<span class="mw-page-title-main">Nadic anhydride</span> Chemical compound

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References

  1. Behr, Arno (2000). "Organometallic Compounds and Homogeneous Catalysis". Ullmann's Encyclopedia of Industrial Chemistry. p. 10. doi:10.1002/14356007.a18_215. ISBN   978-3527306732.
  2. Ballantyne, Bryan; Myers, Roy C.; Klonne, Dennis R. (1997). "Comparative acute toxicity and primary irritancy of the ethylidene and vinyl isomers of norbornene". Journal of Applied Toxicology. 17 (4): 211–221. doi:10.1002/(SICI)1099-1263(199707)17:4<211::AID-JAT430>3.0.CO;2-X. PMID   9285533. S2CID   21154862.