Difference between revisions 6001594 and 6001595 on simplewiki

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| ImageFileL1 = Ferrocene-2D.png
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| ImageFile2 = Photo of Ferrocene (powdered).JPG
(contracted; show full) | doi = 10.1039/DT9960003653
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[[Image:FcGen'l.png|400px|thumb|center|Important reactions of ferrocene with electrophiles and other reagents.]]

===Lithiation===

Ferrocene reacts readily with [[butyl lithium]] to give 1,1'-dilithioferrocene, which in turn is a versatile [[nucleophile]]. 
It has been reported that the reaction of 1,1'-dilithioferrocene with [[selenium]] diethyl[[dithiocarbamate]] forms a strained ferrocenophane where the two cyclopentadienyl ligands are linked by the selenium atom.<ref>Ron Rulkens, Derek P. Gates, David Balaishis, John K. Pudelski, Douglas F. McIntosh, Alan J. Lough, and Ian Manners, ''J. Am. Chem. Soc.'', 1997, '''119''', 10976</ref> This ferrocenophane can be converted to a polymer by a [[thermal]] [[ring-opening polymerization]] (ROP) to form poly(ferrocenyl selenide). Likewise by the reaction of [[silicon]] and [[phosphorus]] linked ferrocenophaThis approach is especially useful method to introduce main group functionality, e.g. using S8, chlorophosphines, chlorosilanes.  Related diphosphines are used as ligands in commerically useful processes.  The strained compounds undergo [[ring-opening polymerization]].<ref>David E. Herbert, Ulrich F. J. Mayer, Ian Manners the poly(ferrocenylsilane)s and poly(ferrocenylphos“Strained Metallocenophianes)s can be obtained.<ref>Paloma Gómez-Elipe, Rui Resendes, Peter M. Macdonald, and Ian Manners, ''J. Am. Chem. Soc.,'' 1998, '''120''', 8348</ref><ref>Timothy J. Peckham, Jason A. Massey, Charles H. Honeyman, and Ian Manners, ''Macromolecules'', 1999, ''32'', 2830</ref>

[[Image:Ferrocenelithiation.png|450px|thumb|center|A diagram showing the lithiation of ferrocene with BuLi, and then the reac and Related Organometallic Rings Containing pi-Hydrocarbon Ligands and Transition-Metal Centers”  Angew. Chem. Int. Ed. Angew Chem. Int. Ed. Engl. 2007, 46, 5060 - 5081.   {{DOI|10.1002/anie.200604409}}</ref>

[[Image:FcLi2chem.png|450px|thumb|center|Some transformations of the dilithioferrocene with a series of electrophiles.]]

===Redox chemistry===
Unlike the majority of hydrocarbons, ferrocene undergoes a one-electron oxidation at a low potential, around 0.5 V ''vs''. a [[saturated calomel electrode]] (SCE). It is also been used as standard in electrochemistry as Fc+/Fc = 0.64 V vs. NHE. Some [[electron]] rich hydrocarbons (e.g., [[aniline]]) also are oxidized at low potentials, but only irreversibly. Oxidation of ferrocene gives a stable cation called ferrocenium. On a preparative scale, the oxidation is(contracted; show full)[[pl:Ferrocen]]
[[ru:Ферроцен]]
[[fi:Ferroseeni]]
[[sv:Ferrocen]]
[[th:เฟอร์โรซีน]]
[[tr:Ferrosen]]
[[ur:Ferrocene]]
[[zh:二茂铁]]