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User:Barras/Ferrocene
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| Watchedfields = changed
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| ImageFileL1 = Ferrocene-2D.png
| ImageSizeL1 = 80 px
| ImageFileR1 = Ferrocene-from-xtal-3D-balls.png
| ImageSizeR1 = 120 px
| ImageFile2 = Photo of Ferrocene (powdered).JPG
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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|volume=168|pages=1039}}</ref> synthesis of ferrocene used the [[Grignard reagent]] cyclopentadienyl magnesium bromide, which can be prepared by reacting [[cyclopentadiene]] with magnesium and [[brom
oethane]] in [[anhydrous]] [[benzene]].  [[Iron(II) chloride]] is then suspended in anhydrous [[diethyl ether]] and added to the Grignard reagent.  The reaction sequence is:

:CH<sub>3</sub>CH<sub>2</sub>Br + Mg + C<sub>5</sub>H<sub>6</sub> &rarr; C<sub>5</sub>H<sub>5</sub>MgBr + CH<sub>3</sub>CH<sub>3</sub>

(contracted; show full)ient preparative methods are generally a modification of the original [[transmetalation]] sequence using either commercially available [[sodium cyclopentadienide]]<ref>{{OrgSynth|title = Ferrocene|author = [[Geoffrey Wilkinson]]|collvol = 4|collvolpages = 473|year = 1963|prep = cv4p0473}}</ref> or freshly [[cracking|cracked]] cyclopentadiene and [[potassium hydroxide]]<ref>Jolly, W. L., The Synthesis and Characterization of Inorganic Compounds, Prentice-Hall: New Jersey, 1970.</ref>
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 with anhydrous iron(II) chloride in ethereal solvents:
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:2 NaC<sub>5</sub>H<sub>5</sub> + FeCl<sub>2</sub> → Fe(C<sub>5</sub>H<sub>5</sub>)<sub>2</sub> + 2 NaCl

:FeCl<sub>2</sub>.4H<sub>2</sub>O + 2 C<sub>5</sub>H<sub>6</sub> + 2 KOH &rarr; Fe(C<sub>5</sub>H<sub>5</sub>)<sub>2</sub> + 2 KCl + 6 H<sub>2</sub>O

[[Image:Ferrocene 3d model 2.png|thumb|right|A space-filling model of ferrocene.]]
(contracted; show full)[[ru:Ферроцен]]
[[fi:Ferroseeni]]
[[sv:Ferrocen]]
[[th:เฟอร์โรซีน]]
[[tr:Ferrosen]]
[[uk:Фероцен]]
[[ur:Ferrocene]]
[[zh:二茂铁]]