Fulvene

Fulvene
Names
IUPAC name
Fulvene
Other names
Pentafulvene, 5-Methylene-1,3-cyclopentadiene
Identifiers
497-20-1 YesY
ChEBI CHEBI:51999 YesY
ChemSpider 120097 YesY
Jmol interactive 3D Image
PubChem 136323
Properties
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).
YesY verify (what is YesYN ?)
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;[1] the parent chemical, fulvene itself, is rarely encountered.[2] Thiele is credited with discovering the scope of the reaction between cyclopentadiene and aldehydes and ketones that yields the brightly coloured fulvene derivatives.[3] Most fulvenes are still prepared by this route, starting from cyclopentadiene or its sodium cyclopentadienyl anionic form.[4]

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.[5] Some Me4Fv complexes are called tuck-in complexes.

η4- and η6-fulvene complexes

See also

References

  1. ↑ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version:  (2006–) "Fulvenes".
  2. ↑ Bergmann, E. D. (1968). "Fulvenes and Substituted Fulvenes". Chemical Reviews 68: 41–84. doi:10.1021/cr60251a002.
  3. ↑ Thiele, J. (1900). "Ueber Ketonreactionen bei dem Cyclopentadiën". Chemische Berichte 33: 666–673. doi:10.1002/cber.190003301113.
  4. ↑ Hafner, K.; Vöpel, K. H.; Ploss, G.; König, C. (1973). "6-(Dimethylamino)fulvene" (PDF). Organic Syntheses Coll. Vol. 5: 431.
  5. ↑ 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.
This article is issued from Wikipedia - version of the Friday, October 30, 2015. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.