Difference between revisions 6001626 and 6001627 on simplewiki

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| ImageFileL1 = Ferrocene-2D.png
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| ImageFileR1 = Ferrocene-from-xtal-3D-balls.png
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| ImageFile2 = Photo of Ferrocene (powdered).JPG
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: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 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}}</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}}</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) &rarr; Fe(C<sub>5</sub>H<sub>5</sub>)<sub>2</sub> + H<sub>2</sub>(g)

(contracted; show full)

Direct transmetalation can also be used to prepare ferrocene from other metallocenes, such as [[manganocene]]:<ref>{{cite journal |last1= Wilkinson|first1= G.|authorlink1= Geoffrey Wilkinson|last2= Cotton|first2= F. A.|last3= Birmingham|first3= J. M.|year= 1956|title= 
On manganese cyclopentadienide and some chemical reactions of neutral bis-cyclopentadienyl metal compounds|journal= J. Inorg. Nucl. Chem.|volume= 2|issue= |pages= 95|url= |doi=10.1016/0022-1902(56)80004-3 }}</ref>

:FeCl<sub>2</sub> + Mn(C<sub>5</sub>H<sub>5</sub>)<sub>2</sub> &rarr; MnCl<sub>2</sub> + Fe(C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>

(contracted; show full)tive) has been shown to be effective when used for the [[kinetic resolution]] of [[racemic]] [[secondary alcohol]]s.<ref>{{cite journal |last1= Ruble|first1= J. C.|last2= Latham|first2= H. A.|last3= Fu|first3= G. C.|year= 1997|title= Effective Kinetic Resolution of Secondary Alcohols with a Planar-Chiral Analogue of 4-(dimethylamino)pyridine. Use of the Fe(C<sub>5</sub>Ph<sub>5</sub>) Group in Asymmetric Catalysis|journal= [[J. Am. Chem. Soc.]]|volume= 119|issue= 6|pages= 1492
-–1493|url= |doi= 10.1021/ja963835b}}</ref>

==Applications of ferrocene and its derivatives==
Ferrocene and its numerous derivatives have no large-scale applications, but have many niche uses that exploit the unusual structure (ligand scaffolds, pharmaceutical candidates), robustness (anti-knock formulations, precursors to materials), and redox (reagents and redox standards).

===Fuel additives===
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Because of the ease of substitution, many structurally unusual ferrocene derivatives have been prepared. For example, the penta(ferrocenyl)cyclopentadienyl ligand,<ref>{{cite journal|author=Y. Yu, A.D. Bond, P. W. Leonard, K. P. C. Vollhardt, G. D. Whitener| title=Syntheses, Structures, and Reactivity of Radial Oligocyclopentadienyl Metal Complexes: Penta(ferrocenyl)cyclopentadienyl and Congeners| journal= [[Angewandte Chemie International Edition]]| volume =45|issue=11| pages= 1794–1799|year=2006|
pmid=16470902| doi=10.1002/anie.200504047}}</ref> features a cyclopentadiene derivatised with five ferrocene substituents.
[[Image:Penta(ferrocenyl)cyclopentadienyl.png|500px|center|Penta(ferrocenyl)cyclopentadienyl ligand]]

[[Image:Hexaferrocenylbenzene-3D-sticks.png|200px|thumb|right|Structure of hexaferrocenylbenzene]]

In '''hexaferrocenylbenzene''', all six positions on a [[benzene]] molecule have ferrocenyl substituents ('''R''').<ref>{{cite journal|title=Hexaferrocenylbenzene|author= Yong Yu, Andrew D. Bond, Philip W. Leonard, Ulrich J. Lorenz, Tatiana V. Timofeeva, K. Peter C. Vollhardt, Glenn D. Whitener and Andrey A. Yakovenko| journal=[[Chemical Communications]]|issue=24| year=2006| pages= 2572–2574|pmid=16779481 |doi=10.1039/b604844g}}</ref> [[X-ray diffraction]] analysis of this compound confirms that the cyclopentadienyl ligands are not co-planar with the benzene core but have alternating [[dihedral angle]]s of +30° and −80°. Due to steric crowding the ferrocenyls are slightly bent with angles of 177° and have elongated C-Fe bonds. The quaternary cyclopentadienyl carbon atoms are also [[pyramidalization|pyramidalized]].<ref>Also, the benzene core has a [[chair conformation]] with dihedral angles of 1(contracted; show full)[[ru:Ферроцен]]
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