Fulvene

Fulvene(Pentafulvene) usually refers to the hydrocarbon (CH=CH)2C=CH2. It is a prototype of a cross-conjugated hydrocarbon.[2] The parent, fulvene itself, is rarely encountered,[3] but substituted derivatives are numerous. They are mainly of interest as ligands and precursors to ligands in organometallic chemistry. They are often yellow.

Fulvene
Names
Preferred IUPAC name
5-Methylidenecyclopenta-1,3-diene[1]
Other names
Fulvene[1]
5-Methylene-1,3-cyclopentadiene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
Properties
C6H6
Molar mass 78.114 g·mol−1
-42.9·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Preparation

Substituted fulvenes are readily prepared by the condensation of cyclopentadiene and aldehydes and ketones:

C5H6 + R2C=O → C4H4C=CR2 + H2O

Thiele is credited with discovering this reaction.[4][5]

Modern synthesis of fulvenes employ buffer systems.[6][7]

Fulvenes

Several types of fulvenes are defined.[8] They are:

Ligand in organometallic chemistry

Fulvenes are common ligands and ligand precursors in organometallic chemistry.[9] 2,3,4,5-Tetramethylfulvene, abbreviated Me4Fv, results from the deprotonation of cationic pentamethylcyclopentadienyl complexes.[10] Some Me4Fv complexes are called tuck-in complexes.

η4- and η6-fulvene complexes

See also

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. Preethanuj Preethalayam; Syam krishnan, K.; Sreeja Thulasi; Sarath Chand,S.; Jomy Joseph; Vijay Nair; Florian Jaroschik; K.V.Radhakrishnan (2017). "Recent Advances in the Chemistry of Pentafulvenes". Chemical Reviews. 117 (5): 3930–3989. doi:10.1021/acs.chemrev.6b00210. PMID 28151643.
  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. (1967). "6-(Dimethylamino)Fulvene". Organic Syntheses. 47: 52. doi:10.15227/orgsyn.047.0052.
  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. Sieverding, Paul; Osterbrink, Johanna; Besson, Claire; Kögerler, Paul (2019-01-18). "Kinetics and mechanism of pyrrolidine buffer-catalyzed fulvene formation". J. Org. Chem. 84 (2): 486–494. doi:10.1021/acs.joc.8b01660. ISSN 0022-3263. PMID 30540466.
  8. IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version:  (2006–) "Fulvenes". doi:10.1351/goldbook.F02550
  9. Strohfeldt, Katja; Tacke, Matthias (2008). "Bioorganometallic fulvene-derived titanocene anti-cancer drugs". Chemical Society Reviews. 37 (6): 1174–87. doi:10.1039/B707310K. PMID 18497930.
  10. 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. Bibcode:2004RuCRv..73..417K. doi:10.1070/RC2004v073n05ABEH000842.
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