Fulvene

Fulvene

Names
Preferred IUPAC name 5-Methylidenecyclopenta-1,3-diene[1]
Other names Fulvene[1] Pentafulvene 5-Methylene-1,3-cyclopentadiene
Identifiers
CAS Number	497-20-1
3D model (Jmol)	Interactive image
ChEBI	CHEBI:51999
ChemSpider	120097
PubChem	136323
InChI InChI=1S/C6H6/c1-6-4-2-3-5-6/h2-5H,1H2 Key: PGTKVMVZBBZCKQ-UHFFFAOYSA-N InChI=1/C6H6/c1-6-4-2-3-5-6/h2-5H,1H2 Key: PGTKVMVZBBZCKQ-UHFFFAOYAV
SMILES C=C1\C=C/C=C1
Properties
Chemical formula	C6H6
Molar mass	78.11 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
verify (what is  ?)
Infobox references

Fulvene is one of several hydrocarbons with the same formula as benzene, C₆H₆. The fulvenes are the class of molecules based on this simple hydrocarbon skeleton;^[2] the parent chemical, fulvene itself, is rarely encountered.^[3] Thiele is credited with discovering the scope of the reaction between cyclopentadiene and aldehydes and ketones that yields the brightly coloured fulvene derivatives.^[4] Most fulvenes are still prepared by this route, starting from cyclopentadiene or its sodium cyclopentadienyl anionic form.^[5] Modern synthesis of fulvenes now employ protic solvents and catalytic amounts of amines which result in much higher yields.^[6]

Ligand in organometallic chemistry

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.^[7] Some Me₄Fv complexes are called tuck-in complexes.

η⁴- and η⁶-fulvene complexes

See also

• Fulvalene
• Methylenecyclopropene

References

1. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 379. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
2. IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version:  (2006–) "Fulvenes".
3. Bergmann, E. D. (1968). "Fulvenes and Substituted Fulvenes". Chemical Reviews. 68: 41–84. doi:10.1021/cr60251a002.
4. Thiele, J. (1900). "Ueber Ketonreactionen bei dem Cyclopentadiën". Chemische Berichte. 33: 666–673. doi:10.1002/cber.190003301113.
5. Hafner, K.; Vöpel, K. H.; Ploss, G.; König, C. (1973). "6-(Dimethylamino)fulvene" (PDF). Organic Syntheses Coll. Vol. 5: 431.
6. Coşkun, Necdet; Erden, Ihsan (2011-11-11). "An efficient catalytic method for fulvene synthesis". Tetrahedron. 67 (45): 8607–8614. doi:10.1016/j.tet.2011.09.036. ISSN 0040-4020. PMC 3196336. PMID 22021940.
7. Kreindlin, A. Z.; Rybinskaya, M. A. (2004). "Cationic and Neutral Transition Metal Complexes with a Tetramethylfulvene or Trimethylallyldiene Ligand". Russian Chemical Reviews. 73 (5): 417–432. doi:10.1070/RC2004v073n05ABEH000842.