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Fulvene

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Fulvene
Names
IUPAC name Fulvene
Other names 5-Methylene-1,3-cyclopentadiene
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
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). checkY 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

  1. Bergmann, E. D. (1968). "Fulvenes and Substituted Fulvenes". Chemical Reviews. 68: 41–84. doi:10.1021/cr60251a002.
  2. Thiele, J. (1900). "Ueber Ketonreactionen bei dem Cyclopentadiën". Chemische Berichte. 33: 666–673. doi:10.1002/cber.190003301113.
  3. 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)
  4. 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)
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