From Surf Wiki (app.surf) — the open knowledge base

Norbornene

Norcamphene |NFPA-H = 2 |NFPA-F = 3 |NFPA-R = 1 |NFPA-S =

Norbornene or norbornylene or norcamphene is a highly strained 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 carbons 1 and 4. The molecule carries a double bond which induces significant ring strain and significant reactivity.

The name comes from norbornane, from bornane.

Production

Norbornene is made by a Diels–Alder reaction of cyclopentadiene and ethylene. Many substituted norbornenes can be prepared similarly. Related bicyclic compounds are norbornadiene, which has the same carbon skeleton but with two double bonds, and norbornane which is prepared by hydrogenation of norbornene.

Reactions

Norbornene undergoes an acid-catalyzed hydration reaction to form norborneol. This reaction was of great interest in the elucidation of the non-classical carbocation controversy.

Norbornene is used in the Catellani reaction and in norbornene-mediated meta-C−H activation.

Certain substituted norbornenes undergo unusual substitution reactions owing to the generation of the 2-norbornyl cation.

Being a strained ene, norbornenes react readily with thiols in the thiol-ene reaction to form thioethers. This makes norbornene-functionalized monomers ideal for polymerization with thiol-based monomers to form thiol-ene networks.

Polynorbornenes

Norbornenes are important monomers in ring-opening metathesis polymerizations (ROMP). Typically these conversions are effected with ill-defined catalysts. Polynorbornenes exhibit high glass transition temperatures and high optical clarity. :[[File:Polynbornene.svg|thumb|center|444px|ROMP reaction giving polynorbornene. Like most commercial alkene metathesis processes, this reaction does not employ a well-defined molecular catalyst.]]

In addition to ROMP, norbornene monomers also undergo vinyl-addition polymerization, and is a popular monomer for use in cyclic olefin copolymers.

Polynorbornene is used mainly in the rubber industry for antivibration (rail, building, industry), antiimpact (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

[https://fscimage.fishersci.com/msds/66955.htm Norbornene MSDS]
"Cyclopropene: A New Simple Synthesis and its Diels-Alder Reaction with Cyclopentadiene".
"2-Cyclohexene-1,4-dione".
Thansandote, Praew. (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.
(2010). "Thiol–Ene Click Chemistry". [[Angewandte Chemie International Edition]].
{{cite encyclopedia. (2005). Wiley-VCH

Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

monomers norbornanes

Want to explore this topic further?

Ask Mako anything about Norbornene — get instant answers, deeper analysis, and related topics.

Research with Mako

Free with your Surf account

Content sourced from Wikipedia, available under CC BY-SA 4.0.

This content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.

Report