Fulvene: Difference between revisions

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Revision as of 07:23, 9 August 2011 editBeetstra (talk \| contribs)Edit filter managers, Administrators172,071 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI').← Previous edit		Revision as of 07:35, 9 August 2011 edit undoCheMoBot (talk \| contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WiNext edit →
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	\| verifiedrevid = ~~400096527~~		\| verifiedrevid = 443828084
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	\| CASNo=497-20-1		\| CASNo=497-20-1
	\| PubChem=136323		\| PubChem=136323
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	\| ChEBI = 51999		\| ChEBI = 51999
	\| SMILES = C=C1\C=C/C=C1		\| SMILES = C=C1\C=C/C=C1
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Revision as of 07:35, 9 August 2011

Fulvene

Names

IUPAC name Fulvene

Other names 5-Methylene-1,3-cyclopentadiene

Identifiers

CAS Number

497-20-1

3D model (JSmol)

Interactive image

ChEBI

CHEBI:51999

ChemSpider

120097

PubChem CID

136323

CompTox Dashboard (EPA)

DTXSID30897602

InChI

InChI=1S/C6H6/c1-6-4-2-3-5-6/h2-5H,1H2Key: PGTKVMVZBBZCKQ-UHFFFAOYSA-N
InChI=1/C6H6/c1-6-4-2-3-5-6/h2-5H,1H2Key: PGTKVMVZBBZCKQ-UHFFFAOYAV

SMILES

C=C1\C=C/C=C1

Properties

Chemical formula

C₆H₆

Molar mass

78.11 g/mol

Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).

Y verify (what is ?) Infobox references

Chemical compound

Fulvene is one of several hydrocarbons with the same formula as benzene, C₆H₆. Fulvenes include the derivatives of this simple hydrocarbon, which itself is rarely encountered. Thiele is credited with discovering the scope of the reaction between cyclopentadiene and aldehydes and ketones that affords the brightly coloured fulvene derivatives. Most fulvenes are prepared by the reactions starting from cyclopentadiene or sodium cyclopentadienyl.

2,3,4,5-Tetramethylfulvene, abbreviated Me₄Fv, is a relatively common ligand in organometallic chemistry. It typically results from the deprotonation of cationic pentamethylcyclopentadienyl complexes.

References

Bergmann, E. D. (1968). "Fulvenes and Substituted Fulvenes". Chemical Reviews. 68: 41–84. doi:10.1021/cr60251a002.
Thiele, J. (1900). "Ueber Ketonreactionen bei dem Cyclopentadiën". Chemische Berichte. 33: 666–673. doi:10.1002/cber.190003301113.
Hafner, K.; Vöpel, K. H.; Ploss, G.; König, C. (1973). "6-(Dimethylamino)fulvene" (PDF). Organic Syntheses Coll. Vol. 5: 431.{{cite journal}}: CS1 maint: multiple names: authors list (link)
Kreindlin, A. Z.; Rybinskaya, M. A. (2004). "Cationic and Neutral Transition Metal Complexes with a Tetramethylfulvene or Trimethylallyldiene Ligand". Russian Chemical Reviews. 73: 417–432. doi:10.1070/RC2004v073n05ABEH000842.{{cite journal}}: CS1 maint: multiple names: authors list (link)

Category:

Hydrocarbons