Norbornene
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| Names | |||
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| Preferred IUPAC name
Bicyclo[2.2.1]hept-2-ene | |||
| Other names
Norbornylene
Norcamphene | |||
| Identifiers | |||
3D model (JSmol)
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| ChemSpider | |||
| ECHA InfoCard | 100.007.152 | ||
| EC Number |
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |||
| C7H10 | |||
| Molar mass | 94.157 g·mol−1 | ||
| Appearance | White solid | ||
| Melting point | 42 to 46 °C (108 to 115 °F; 315 to 319 K) | ||
| Boiling point | 96 °C (205 °F; 369 K) | ||
| Hazards | |||
| NFPA 704 (fire diamond) | |||
| Flash point | −15 °C (5 °F; 258 K) | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Norbornene or norbornylene or norcamphene is a bridged cyclic hydrocarbon. It is a white solid with a pungent sour odor. The molecule consists of a cyclohexene ring with a methylene bridge between C-3 and C-6. The molecule carries a double bond which induces significant ring strain and significant reactivity.
Norbornene, like many of its derivatives, is made by a Diels-Alder reaction of cyclopentadiene and ethylene.[2][3] Related bicyclics are norbornadiene which has the same carbon skeleton but with two double bonds and norbornane which is completely saturated without double bonds.
Norbornene undergoes an acid-catalyzed hydration reaction with water to form norborneol. This reaction is of great interest to chemists studying non-classical ions.
Uses
Norbornene does not have as many practical uses as ethylene or other commodity chemicals. It is utilized to make pharmaceutical intermediates, pesticide compounds, specialty fragrances and in general organic synthesis. When combined with ethylene, norbornene will react and turn into a cyclic olefin copolymer.
Norbornene is commonly used in transition metal catalysis to effect the migration of electrophilic transition metals. This reactivity is prominently exploited in the Catellani reaction and in norbornene-mediated meta-C-H activation.[4] It is also commonly used in transition metal catalysis as a sacrificial hydrogen acceptor.[citation needed]
Polynorbornenes
Norbornenes are important monomers in ring-opening metathesis polymerizations (ROMP) with for instance the Grubbs' catalyst. Polynorbornenes are polymers with high glass transition temperatures and high optical clarity.[5]
In addition to ROMP polymerization, norbornene monomers also undergo vinyl-addition polymerization.
Polynorbornene is used mainly in the rubber industry for anti-vibration (rail, building, industry), anti-impact (personal protective equipment, shoe parts, bumpers) and grip improvement (toy tires, racing tires, transmission systems, transports systems for copiers, feeders, etc.)
Ethylidene norbornene is a related monomer derived from cyclopentadiene and butadiene.
References
- ^ Norbornene MSDS
- ^ Paul Binger, Petra Wedemann, and Udo H. Brinker. "Cyclopropene: A New Simple Synthesis and its Diels-Alder Reaction with Cyclopentadiene". Organic Syntheses
{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 10, p. 231. - ^ Masaji Oda, Takeshi Kawase, Tomoaki Okada, and Tetsuya Enomoto. "2-Cyclohexene-1,4-dione". Organic Syntheses
{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 9, p. 186. - ^ Thansandote, Praew; Chong, Eugene; Feldmann, Kai-Oliver; Lautens, Mark (21 May 2010). "Palladium-Catalyzed Domino C−C/C−N Coupling Using a Norbornene Template: Synthesis of Substituted Benzomorpholines, Phenoxazines, and Dihydrodibenzoxazepines". The Journal of Organic Chemistry. 75 (10): 3495–3498. doi:10.1021/jo100408p. PMID 20423091.
- ^ Mol, J. C. Journal of Molecular Catalysis A: Chemical 2004, 213 (2), 39-45.