| Revision as of 06:40, 15 September 2011 editAmirobot (talk | contribs)56,602 editsm r2.7.1) (robot Adding: it:Norbornene← Previous edit |
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{{chembox |
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| verifiedrevid = 402510449 |
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|verifiedrevid = 450599059 |
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| Reference = <ref></ref> |
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|Reference = <ref></ref> |
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| ImageFileL1 = Norbornene.png |
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|ImageFileL1 = Norbornene.png |
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| ImageSizeL1 = 100px |
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| ImageFileR1 = Norbornene2.png |
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|ImageFileR1 = Norbornene2.png |
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|ImageFile2 = Norbornene3.png |
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| ImageSizeR1 = 120px |
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|ImageSize2 = 150px |
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| ImageFile2 = Norbornene3.png |
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|PIN = Bicyclohept-2-ene <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) --> |
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| ImageSize2 = 150px |
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|OtherNames = Norbornylene<br>Norcamphene |
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| IUPACName = Bicyclohept-2-ene |
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|Section1={{Chembox Identifiers |
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| OtherNames = Norbornylene<br>Norcamphene |
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|PubChem = 10352 |
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| Section1 = {{Chembox Identifiers |
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|ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| Abbreviations = |
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|ChemSpiderID = 9925 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|InChI = 1/C7H10/c1-2-7-4-3-6(1)5-7/h1-2,6-7H,3-5H2 |
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| ChemSpiderID = 10606238 |
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|InChIKey = JFNLZVQOOSMTJK-UHFFFAOYAB |
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| InChI1 = 1/C7H10/c1-2-7-4-3-6(1)5-7/h1,7H,2-5H2 |
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|StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| InChIKey1 = VGUXWSJVGWCTEC-UHFFFAOYAW |
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|StdInChI = 1S/C7H10/c1-2-7-4-3-6(1)5-7/h1-2,6-7H,3-5H2 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C7H10/c1-2-7-4-3-6(1)5-7/h1,7H,2-5H2 |
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|StdInChIKey = JFNLZVQOOSMTJK-UHFFFAOYSA-N |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| StdInChIKey = VGUXWSJVGWCTEC-UHFFFAOYSA-N |
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|CASNo = 498-66-8 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| CASNo = 498-66-8 |
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|UNII = 2Q51FLS550 |
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| EINECS = 207-866-0 |
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|EINECS = 207-866-0 |
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| PubChem = 10352 |
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| SMILES = C1/C2=C\CC1CC2 |
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|SMILES = C1=CC2CCC1C2 |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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| InChI = 1/C7H10/c1-2-7-4-3-6(1)5-7/h1-2,6-7H,3-5H2 |
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|ChEBI = 52286 |
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|Section2={{Chembox Properties |
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| C=7 | H=10 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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|Appearance = White solid |
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| KEGG = |
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|MeltingPtC = 42 to 46 |
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|BoilingPtC = 96 |
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| Section2 = {{Chembox Properties |
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|Section7={{Chembox Hazards |
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|NFPA-H = 2 |
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| C=7|H=10 |
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|NFPA-F = 3 |
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| Appearance = White solid |
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| Density = |
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|NFPA-R = 1 |
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|NFPA-S = |
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| MeltingPtCL = 42 |
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|FlashPtC = −15 |
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| MeltingPtCH = 46 |
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|OtherCompounds = ] |
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| NFPA-H = 2 |
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| NFPA-F = 3 |
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| NFPA-R = 1 |
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| FlashPt = −15 °C |
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'''Norbornene''' or '''norbornylene''' or '''norcamphene''' is a bridged cyclic ]. It is a white solid with a pungent sour odor. The ] consists of a ] ring bridged with a ] group in the ]. The molecule carries a ] which induces significant ] and significant reactivity. |
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'''Norbornene''' or '''norbornylene''' or '''norcamphene''' is a highly strained bridged cyclic ]. It is a white solid with a pungent sour odor. The ] consists of a ] ring with a ] between carbons 1 and 4. The molecule carries a ] which induces significant ] and significant reactivity. |
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==Production== |
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Norbornene, like many of its derivatives, is made by a ] of ] and ].<ref>{{OrgSynth | author = Paul Binger, Petra Wedemann, and Udo H. Brinker| title = Cyclopropene: A New Simple Synthesis and its Diels-Alder Reaction with Cyclopentadiene | collvol = 10 | collvolpages = 231 | prep=v77p0254}}</ref><ref>{{OrgSynth | author = Masaji Oda, Takeshi Kawase, Tomoaki Okada, and Tetsuya Enomoto | title = 2-Cyclohexene-1,4-dione | collvol = 9 | collvolpages = 186 | prep = cv9p0186}}</ref> Related bicyclics are ] which has the same carbon skeleton but with two double bonds and ] which is completely saturated without double bonds. |
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Norbornene is made by a ] of ] and ]. Many substituted norbornenes can be prepared similarly.<ref>{{OrgSynth | first1= Paul |last1=Binger |first2=Petra |last2=Wedemann |first3=Udo H. |last3=Brinker| title = Cyclopropene: A New Simple Synthesis and its Diels-Alder Reaction with Cyclopentadiene | collvol = 10 | collvolpages = 231 | prep=v77p0254}}</ref><ref>{{OrgSynth | first1=Masaji |last1=Oda |first2=Takeshi |last2=Kawase |first3=Tomoaki |last3=Okada |first4=Tetsuya |last4=Enomoto | title = 2-Cyclohexene-1,4-dione | collvol = 9 | collvolpages = 186 | prep = cv9p0186}}</ref> Related bicyclic compounds are ], which has the same carbon skeleton but with two double bonds, and ] which is prepared by ] of norbornene. |
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== Reactions == |
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Norbornene undergoes an acid-catalyzed ] with water to form ]. This reaction is of great interest to chemists studying ]s. |
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Norbornene undergoes an acid-catalyzed ] to form ]. This reaction was of great interest in the elucidation of the ]. |
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Norbornene is used in the ] and in norbornene-mediated ''meta''-C−H activation.<ref>{{cite journal|last=Thansandote|first=Praew|date=21 May 2010|title=Palladium-Catalyzed Domino C−C/C−N Coupling Using a Norbornene Template: Synthesis of Substituted Benzomorpholines, Phenoxazines, and Dihydrodibenzoxazepines|journal=The Journal of Organic Chemistry|volume=75|issue=10|pages=3495–3498|doi=10.1021/jo100408p|pmid=20423091|last2=Chong|first2=Eugene|last3=Feldmann|first3=Kai-Oliver|last4=Lautens|first4=Mark}}</ref> |
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== Polynorbornenes == |
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Norbornenes are important ]s in ]s (ROMP) with for instance the ]. '''Polynorbornenes''' are ]s with high ]s and high optical clarity. |
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Certain substituted norbornenes undergo unusual substitution reactions owing to the generation of the ]. |
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Being a strained ene, norbornenes react readily with ]s in the ] to form ]s. This makes norbornene-functionalized monomers ideal for polymerization with thiol-based monomers to form thiol-ene networks.<ref>{{cite journal |last1=Hoyle |first1=Charles E. |last2=Bowman |first2=Christopher N. |title=Thiol–Ene Click Chemistry |journal=] |year=2010 |volume=49 |issue=9 |doi=10.1002/anie.200903924 |pages=1540–1573}}</ref> |
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In addition to ROMP polymerization, norbornene monomers also undergo ]. |
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===Polynorbornenes=== |
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] is a related monomer derived from ] and ]. |
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Norbornenes are important ]s in ]s (ROMP). Typically these conversions are effected with ill-defined catalysts. '''Polynorbornenes''' exhibit high ]s and high optical clarity.<ref name=KO>{{cite encyclopedia|encyclopedia=Kirk-Othmer Encyclopedia of Chemical Technology|first1=Lionel |last1=Delaude |first2=Alfred F. |last2=Noels|year=2005| doi=10.1002/0471238961.metanoel.a01|place=Weinheim|publisher=Wiley-VCH|isbn = 978-0471238966|chapter = Metathesis}}</ref> |
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In addition to ROMP, norbornene monomers also undergo vinyl-], and is a popular monomer for use in ]s. |
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== Practical uses == |
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Norbornene does not have as many practical uses as ] 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 ]. |
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'''Polynorbornene''', known under Norsorex, a brand from Astrotech Advanced Elastomerproducts GmbH since 2008, 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.) |
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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.) |
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*Reachable performances: Loss factors (tan delta) larger than 3, rebounds of less than 1%, tear strengths of 50 N/mm², friction coefficients of 2 and more, ] between 4 and 90 Shore A. |
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] is a related monomer derived from ] and ]. |
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*Second main application: oil-binding system with absorption capability of hydrocarbons, 10 times of own weight |
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==See also== |
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*] |
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==References== |
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==References== |
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{{Reflist}} |
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{{Reflist|30em}} |
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{{Authority control}} |
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