Difference between revisions 6001617 and 6001618 on simplewiki

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| 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==

Ferrocene is efficiently prepared by the reaction of [[sodiumThe 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 [[bromethane]] 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>

:2 C<sub>5</sub>H<sub>5</sub>MgBr + FeCl<sub>2</sub> &rarr; 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 cyclopentadienide]]e with anhydrous [[iron(II) chloride]] metallic iron<ref>{{cite journal|year=1954|last1=Wilkinson|first1=G.|last2=Pauson|first2=P. L.|last3=Cotton|first3=F. A.|journal=Journal of the American Chemical Society|volume=76|pages=1970}}</ref> at 623 K and with [[iron pentacarbonyl]].<ref>{{cite journal|year=1959|last1=Wilkinson|first1=G.|last2=Cotton|first2=F. A.|journal=Progress in Inorganic Chemistry|volume=1|pages=1-124}}</ref>

:Fe + 2 C<sub>5</sub>H<sub>6</sub>(g) &rarr; Fe(C<sub>5</sub>H<sub>5</sub>)<sub>2</sub> + H<sub>2</sub>(g)

:Fe(CO)<sub>5</sub> + 2 C<sub>5</sub>H<sub>6</sub>(g) &rarr; Fe(C<sub>5</sub>H<sub>5</sub>)<sub>2</sub> + 5 CO(g) + H<sub>2</sub>(g)

Modern and more efficient preparative methods are generally a modification of the original [[transmetalation]] sequence using eithereal solvents: commercially available [[sodium cyclopentadienide]]<ref>{{OrgSynth|title = Ferrocene|author = [[Geoffrey Wilkinson]]|collvol = 4|collvolpages = 473|year = 1963|prep = cv4p0473}}</ref>⏎
: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 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>
 with anhydrous iron(II) chloride in ethereal solvents:
: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.]]
As expected for a symmetric and uncharged species, ferrocene is soluble in normal organic solvents, such as benzene, but is insoluble in water. Ferrocene is an [[air]]-stable orange solid that readily [[Sublimation (physics)|sublime]]s, especially upon heating in a vacuum. It is stable to temperatures as high as 400 °C.<ref>Solomons, Graham, and Craig Fryhle. Organic Chemistry. 9th ed. USA: John Wiley & Sons, Inc.,(contracted; show full)[[ru:Ферроцен]]
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