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Revision as of 07:23, 9 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI').← Previous edit Latest revision as of 22:12, 3 September 2024 edit undoBD2412 (talk | contribs)Autopatrolled, IP block exemptions, Administrators2,453,387 editsm →top: Clean up spacing around commas and other punctuation fixes, replaced: ,S → , STag: AWB 
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{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 400096527 | verifiedrevid = 443829334
⚫ |ImageFileL1=Fulvene.png
| Name =
⚫ |ImageSizeL1=120px
| ImageFile =
⚫ |ImageFileR1=Fulvene_3D.png
⚫ | ImageFileL1 = Fulvene with hydrogens.svg
⚫ |ImageSizeR1=120px
⚫ | ImageSizeL1 = 120px
⚫ |IUPACName=Fulvene
⚫ | ImageFileR1 = Fulvene_3D.png
⚫ |OtherNames=5-Methylene-1,3-cyclopentadiene
⚫ | ImageSizeR1 = 120px
⚫ |Section1={{Chembox Identifiers
| PIN = 5-Methylidenecyclopenta-1,3-diene<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 379 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref>
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| SystematicName =
⚫ | OtherNames = Fulvene<ref name=iupac2013 /><br />5-Methylene-1,3-cyclopentadiene
⚫ | IUPACName =
⚫ | Section1 = {{Chembox Identifiers
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 120097 | ChemSpiderID = 120097
| InChI = 1/C6H6/c1-6-4-2-3-5-6/h2-5H,1H2 | InChI = 1/C6H6/c1-6-4-2-3-5-6/h2-5H,1H2
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = PGTKVMVZBBZCKQ-UHFFFAOYSA-N | StdInChIKey = PGTKVMVZBBZCKQ-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=497-20-1 | CASNo=497-20-1
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem=136323
| ChEBI = 51999 | UNII = 19W699IKIE
⚫ | PubChem=136323
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 51999
| SMILES = C=C1\C=C/C=C1 | SMILES = C=C1\C=C/C=C1
}} }}
|Section2={{Chembox Properties | Section2 = {{Chembox Properties
| C=6|H=6
| Formula=C<sub>6</sub>H<sub>6</sub>
| Appearance=
| MolarMass=78.11 g/mol
| Appearance= | Density=
| Density= | MeltingPt=
| MeltingPt= | BoilingPt=
| BoilingPt= | Solubility=
| MagSus = -42.9·10<sup>−6</sup> cm<sup>3</sup>/mol
| Solubility=
}} }}
|Section3={{Chembox Hazards | Section3 = {{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
| Section4 =
| Section5 =
| Section6 =
}} }}
'''Fulvene''' (pentafulvene) is a ] with the formula (CH=CH)<sub>2</sub>C=CH<sub>2</sub>. It is a prototype of a ] hydrocarbon.<ref>{{cite journal|author1=Preethanuj Preethalayam |author2=Syam krishnan, K.|author3=Sreeja Thulasi |author4= Sarath Chand, S. |author5=Jomy Joseph

|author6= Vijay Nair
'''Fulvene''' is one of several ]s with the same formula as ], C<sub>6</sub>H<sub>6</sub>. Fulvenes include the derivatives of this simple hydrocarbon, which itself is rarely encountered.<ref>{{cite journal
|author7=Florian Jaroschik|author8=K.V.Radhakrishnan
|title= Recent Advances in the Chemistry of Pentafulvenes.
⚫ |journal = Chemical Reviews
|year=2017|volume= 117|issue=5|pages= 3930–3989
|doi=10.1021/acs.chemrev.6b00210|pmid=28151643}}</ref> Fulvene is rarely encountered,<ref>{{cite journal
| author = Bergmann, E. D. | author = Bergmann, E. D.
| title = Fulvenes and Substituted Fulvenes | title = Fulvenes and Substituted Fulvenes
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| pages = 41–84 | pages = 41–84
| year = 1968 | year = 1968
| doi = 10.1021/cr60251a002}}</ref> ] is credited with discovering the scope of the reaction between ] and ]s and ]s that affords the brightly coloured fulvene derivatives.<ref>{{cite journal | doi = 10.1021/cr60251a002}}</ref> but substituted derivatives (]) are numerous. They are mainly of interest as ]s and precursors to ligands in ].

| author = Thiele, J.
Fulvene is an isomer of ], which when irradiated at 237 to 254&nbsp;nm forms small amounts of fulvene along with ].<ref>{{Cite journal |last=Kaplan |first=Louis |last2=Wilzbach |first2=K. E. |date=1968 |title=Photolysis of benzene vapor. Benzvalene formation at wavelengths 2537-2370 A |url=https://pubs.acs.org/doi/abs/10.1021/ja01014a086 |journal=Journal of the American Chemical Society |language=en |volume=90 |issue=12 |pages=3291–3292 |doi=10.1021/ja01014a086 |issn=0002-7863}}</ref>
| title = <!--no umlaut-->Ueber Ketonreactionen bei dem Cyclopentadiën
| journal = ]
| volume = 33
| pages = 666–673
| year = 1900
| doi = 10.1002/cber.190003301113}}</ref> Most fulvenes are prepared by the reactions starting from cyclopentadiene or sodium cyclopentadienyl.<ref>{{cite journal
| author = Hafner, K.; Vöpel, K. H.; Ploss, G.; König, C.
| title = 6-(Dimethylamino)fulvene
| journal = Organic Syntheses Coll. Vol.
| volume = 5
| pages = 431
| year = 1973
| url = http://www.orgsyn.org/orgsyn/pdfs/CV5P0431.pdf}}</ref>


== See also ==
2,3,4,5-Tetramethylfulvene, abbreviated Me<sub>4</sub>Fv, is a relatively common ligand in ]. It typically results from the deprotonation of cationic ] complexes.<ref>{{cite journal
*]
| author = Kreindlin, A. Z.; Rybinskaya, M. A.
*]
| title = Cationic and Neutral Transition Metal Complexes with a Tetramethylfulvene or Trimethylallyldiene Ligand
⚫ | journal = Russian Chemical Reviews
| volume = 73
| pages = 417–432
| year = 2004
| doi = 10.1070/RC2004v073n05ABEH000842}}</ref>


==References== ==References==
{{reflist}} {{reflist}}


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