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Wikipedia

Norbornene

January 01, 1970

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.

Norbornene[1]
Names
Preferred IUPAC name
Bicyclo[2.2.1]hept-2-ene
Other names
Norbornylene
Norcamphene
Identifiers
  • 498-66-8 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:52286 Y
ChemSpider
  • 9925 N
ECHA InfoCard 100.007.152
EC Number
  • 207-866-0
  • 10352
UNII
  • 2Q51FLS550 Y
  • DTXSID2022042
  • InChI=1S/C7H10/c1-2-7-4-3-6(1)5-7/h1-2,6-7H,3-5H2 N
    Key: JFNLZVQOOSMTJK-UHFFFAOYSA-N N
  • InChI=1/C7H10/c1-2-7-4-3-6(1)5-7/h1-2,6-7H,3-5H2
    Key: JFNLZVQOOSMTJK-UHFFFAOYAB
  • C1=CC2CCC1C2
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)
Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2
3
1
Flash point −15 °C (5 °F; 258 K)
Related compounds
Related compounds
 Nadic anhydride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

Production edit

Norbornene is made by a Diels–Alder reaction of cyclopentadiene and ethylene. Many substituted norbornenes can be prepared similarly.[2][3] 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 edit

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

Norbornene is used in the Catellani reaction and in norbornene-mediated meta-C−H activation.[4]

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.[5]

Polynorbornenes edit

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.[6]

 
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.

See also edit

References edit

  1. ^ Norbornene MSDS
  2. ^ Binger, Paul; Wedemann, Petra; Brinker, Udo H. "Cyclopropene: A New Simple Synthesis and its Diels-Alder Reaction with Cyclopentadiene". Organic Syntheses; Collected Volumes, vol. 10, p. 231.
  3. ^ Oda, Masaji; Kawase, Takeshi; Okada, Tomoaki; Enomoto, Tetsuya. "2-Cyclohexene-1,4-dione". Organic Syntheses; Collected Volumes, vol. 9, p. 186.
  4. ^ 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.
  5. ^ Hoyle, Charles E.; Bowman, Christopher N. (2010). "Thiol–Ene Click Chemistry". Angewandte Chemie International Edition. 49 (9): 1540–1573. doi:10.1002/anie.200903924.
  6. ^ Delaude, Lionel; Noels, Alfred F. (2005). "Metathesis". Kirk-Othmer Encyclopedia of Chemical Technology. Weinheim: Wiley-VCH. doi:10.1002/0471238961.metanoel.a01. ISBN 978-0471238966.

January 01, 1970
norbornene, norbornylene, norcamphene, highly, strained, bridged, cyclic, hydrocarbon, white, solid, with, pungent, sour, odor, molecule, consists, cyclohexene, ring, with, methylene, bridge, between, carbons, molecule, carries, double, bond, which, induces, 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 Norbornene 1 Names Preferred IUPAC name Bicyclo 2 2 1 hept 2 ene Other names NorbornyleneNorcamphene Identifiers CAS Number 498 66 8 Y 3D model JSmol Interactive image ChEBI CHEBI 52286 Y ChemSpider 9925 N ECHA InfoCard 100 007 152 EC Number 207 866 0 PubChem CID 10352 UNII 2Q51FLS550 Y CompTox Dashboard EPA DTXSID2022042 InChI InChI 1S C7H10 c1 2 7 4 3 6 1 5 7 h1 2 6 7H 3 5H2 NKey JFNLZVQOOSMTJK UHFFFAOYSA N NInChI 1 C7H10 c1 2 7 4 3 6 1 5 7 h1 2 6 7H 3 5H2Key JFNLZVQOOSMTJK UHFFFAOYAB SMILES C1 CC2CCC1C2 Properties Chemical formula C 7H 10 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 231 Flash point 15 C 5 F 258 K Related compounds Related compounds Nadic anhydride Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Production 2 Reactions 2 1 Polynorbornenes 3 See also 4 ReferencesProduction editNorbornene is made by a Diels Alder reaction of cyclopentadiene and ethylene Many substituted norbornenes can be prepared similarly 2 3 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 editNorbornene undergoes an acid catalyzed hydration reaction to form norborneol This reaction was of great interest in the elucidation of the non classical carbonion controversy Norbornene is used in the Catellani reaction and in norbornene mediated meta C H activation 4 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 5 Polynorbornenes edit 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 6 nbsp 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 See also editNadic anhydrideReferences edit Norbornene MSDS Binger Paul Wedemann Petra Brinker Udo H Cyclopropene A New Simple Synthesis and its Diels Alder Reaction with Cyclopentadiene Organic Syntheses Collected Volumes vol 10 p 231 Oda Masaji Kawase Takeshi Okada Tomoaki Enomoto Tetsuya 2 Cyclohexene 1 4 dione Organic Syntheses 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 Hoyle Charles E Bowman Christopher N 2010 Thiol Ene Click Chemistry Angewandte Chemie International Edition 49 9 1540 1573 doi 10 1002 anie 200903924 Delaude Lionel Noels Alfred F 2005 Metathesis Kirk Othmer Encyclopedia of Chemical Technology Weinheim Wiley VCH doi 10 1002 0471238961 metanoel a01 ISBN 978 0471238966 Retrieved from https en wikipedia org w index php title Norbornene amp oldid 1193660014, wikipedia, wiki, book, books, library,

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