Difference between revisions 6001682 and 6001683 on simplewiki

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| ImageFileL1 = Ferrocene.svg
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| ImageFileR1 = Ferrocene-from-xtal-3D-balls.png
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| ImageFile2 = Photo of Ferrocene (powdered).JPG
(contracted; show full)overed ferrocene: {{cite journal|author=S. A. Miller, J. A. Tebboth, and J. F. Tremaine |year=1952|title=Dicyclopentadienyliron|journal=Journal of the Chemical Society|pages =632–635}}</ref><ref name=r1>{{cite journal|author = Pierre Laszlo, Roald Hoffmann,|title = Ferrocene: Ironclad History or Rashomon Tale? |journal = Angewandte Chemie International Edition |year = 2000 |volume = 39 |pages = 123–124 |doi = 10.1002/(SICI)1521-3773(20000103)39:1<123::AID-ANIE123>3.0.CO;2-Z |pmid=10649350
|issue = 1}}</ref> This stability was accorded to the aromatic character of the negative charged cyclopentadienyls, but the sandwich structure of the η<sup>5</sup> (pentahapto) compound was not recognized by them.

(contracted; show full)1-Undecanethiol on Highly Oriented Pyrolitic Graphite Characterized by Scanning Tunneling Microscopy |journal = E-Journal of Surface Science and Nanotechnology |year = 2008 |volume = 6 |pages = 119–123 |doi = 10.1380/ejssnt.2008.119}}</ref><ref>{{cite journal|doi=10.1380/ejssnt.2008.119|url=http://www.jstage.jst.go.jp/article/ejssnt/6/0/119/_pdf |title=Self-Assembling Properties of 11-Ferrocenyl-1-Undecanethiol on Highly Oriented Pyrolitic Graphite Characterized by Scanning Tunneling Microscopy
|year=2008|last1=Qune|first1=Lloyd F. N. Ah|last2=Tamada|first2=Kaoru|last3=Hara|first3=Masahiko|journal=E-Journal of Surface Science and Nanotechnology|volume=6|pages=119}}</ref>

The carbon-carbon bond distances are 1.40 Å within the five membered rings, and the Fe-C bond distances are 2.04 Å.

==Synthesis and handling properties==
The first reported<ref>{{cite journal|year=1951|last1=Kealy|first1=T. J.|last2=Pauson|first2=P. L.|journal=[[Nature (journal)|Nature]]|volume=168|pages=1039|doi=10.1038/1681039b0|issue=4285|title=A New Type of Organo-Iron Compound}}</ref> synthesis of ferrocene used the [[Grignard reaction|Grignard reagent]] cyclopentadienyl magnesium bromide, which can be prepared by reacting [[cyclopentadiene]] with magnesium and [[bromoethane]] in [[anhydrous]] [[benzene]]. [[Iron(II) chloride]] is then suspended in anhydrous [[diethyl ether]] and added to the Grignard reagent. The reaction sequence is:

:2 C<sub>5</sub>H<sub>5</sub>MgBr + FeCl<sub>2</sub> → Fe(C<sub>5</sub>H<sub>5</sub>)<sub>2</sub> + MgCl<sub>2</sub> + MgBr<sub>2</sub>

Numerous other syntheses have been reported, including the direct reaction of [[gas]]-phase cyclopentadiene with metallic iron<ref>{{cite journal|doi=10.1021/ja01636a080|year=1954|last1=Wilkinson|first1=G.|authorlink1=Geoffrey Wilkinson|last2=Pauson|first2=P. L.|last3=Cotton|first3=F. A.|journal=[[J. Am. Chem. Soc.]]|volume=76|pages=1970|issue=7}}</ref> at 350 °C or with [[iron pentacarbonyl]].<ref>{{cite journal|doi=10.1002/9780470166024.ch1|year=1959|last1=Wilkinson|first1=G.|authorlink1=Geoffrey Wilkinson|last2=Cotton|first2=F. A.|title=Cyclopentadienyl and Arene Metal Compounds|journal=Progress in Inorganic Chemistry|volume=1|pages=1–124|series=Progress in Inorganic Chemistry|isbn=9780470166024}}</ref>
[[Image:Ferrocene 3d model 2.png|thumb|right|A space-filling model of the [[staggered conformation]] of ferrocene.]]

:Fe + 2 C<sub>5</sub>H<sub>6</sub>(g) → Fe(C<sub>5</sub>H<sub>5</sub>)<sub>2</sub> + H<sub>2</sub>(g)

(contracted; show full)

===Lithiation===
Ferrocene reacts readily with [[Butyllithium|butyl lithium]] to give 1,1'-dilithioferrocene, which in turn is a versatile [[nucleophile]]. But reaction of Ferrocene with [[Tert-Butyllithium|t-BuLi]] produces monolithioferrocene only.<ref>{{cite journal|title=A convenient method for the preparation of monolithioferrocene|journal= Tetrahedron Letters |volume =31|issue =22|year= 1990|pages =3121–3124|doi=10.1016/S0040-4039(00)94710-5
|last1=Rebiere|first1=F|last2=Samuel|first2=O|last3=Kagan|first3=H.B}}</ref> These approaches are especially useful methods to introduce main group functionality, e.g. using S8, chlorophosphines, chlorosilanes. The strained compounds undergo [[ring-opening polymerization]].<ref>{{cite journal|author=David E. Herbert, Ulrich F. J. Mayer, Ian Manners |title=Strained Metallocenophanes and Related Organometallic Rings Containing pi-Hydrocarbon Ligands and Transition-Metal Centers|journal= Angew. Chem. Int. Ed. |year=2007|volume =46|pages= 5060–5081|doi=10.1002/anie.200604409|issue=27}}</ref>

[[Image:FcLi2chem.png|450px|thumb|center|Some transformations of dilithioferrocene.]]

===Phosphorus derivatives===
Many phosphine derivatives of ferrocenes are known and some are used in commercialized processes.<ref name=Stepnicka>Petr Stepnicka "Ferrocenes: Ligands, Materials and Biomolecules" J. Wiley, Hoboken, 2008. ISBN 0470035854</ref> Simplest and best known is [[1,1'-bis(diphenylphosphino)ferrocene]] (dppf) prepared from dilithioferrocene. For example, in (contracted; show full)

===Materials chemistry===
Ferrocene, being readily decomposed to iron nanoparticles, can be used as a catalyst for the production of carbon nanotubes.<ref>{{cite journal|author=Devin Conroya, Anna Moisalab, Silvana Cardosoa, Alan Windleb and John Davidson|journal=Chemical Engineering Science|year=2010|volume=65|pages=2965–2977
|doi=10.1016/j.ces.2010.01.019|title=Carbon nanotube reactor: Ferrocene decomposition, iron particle growth, nanotube aggregation and scale-up|issue=10}}</ref> The [[vinyl]] ferrocene from ferrocene can be made by a [[Wittig reaction]] of the [[aldehyde]], a [[phosphonium salt]] and [[sodium hydroxide]].<ref>{{cite journal|author=Liu, Wan-yi; Xu, Qi-hai; Ma, Yong-xiang; Liang, Yong-min; Dong, Ning-li; Guan, De-peng|journal=J. Organomet. Chem.|year=2001|volume=625|pages=128–132|doi=10.1016/S0022-328X(00)00927-X|title=Solvent-free synthesis of ferrocenylethene derivatives}}</ref> The vinyl ferrocene can be converted into a polymer which can be thought of as a ferrocenyl version of [[polystyrene]] (the phenyl groups are replaced with ferrocenyl groups).

===As a ligand scaffold===
(contracted; show full);-C<sub>4</sub>H<sub>4</sub>N) ("[[azaferrocene]]"). Azaferrocene arises from decarbonylation of Fe(η<sup>5</sup>-C<sub>5</sub>H<sub>5</sub>)(CO)<sub>2</sub>(η<sup>1</sup>-pyrrole) in [[cyclohexane]].<ref>{{cite journal|doi=10.1016/0022-328X(90)85359-7|title=An improved photochemical synthesis of azaferrocene|year=1990|last1=Zakrzewski|first1=J|journal=Journal of Organometallic Chemistry|volume=388|pages=175
|last2=Giannotti|first2=Charles}}</ref> This compound on boiling under [[reflux]] in [[benzene]] is converted to ferrocene.<ref>{{cite journal|doi=10.1021/ic00133a006|title=Chemistry of some .eta.5-pyrrolyl- and .eta.1-N-pyrrolyliron complexes |year=1982 |last1=Efraty |first1=Avi. |last2=Jubran |first2=Nusrallah |last3=Goldman |first3=Alexander |journal=Inorganic Chemistry|volume=21|pages=868|issue=3}}</ref>

(contracted; show full)[[ru:Ферроцен]]
[[fi:Ferroseeni]]
[[sv:Ferrocen]]
[[th:เฟอร์โรซีน]]
[[tr:Ferrosen]]
[[uk:Фероцен]]
[[ur:Ferrocene]]
[[zh:二茂铁]]