Difference between revisions 6001777 and 6001778 on simplewiki

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 457631192
| ImageFileL1 = Ferrocene.svg
| ImageSizeL1 = 80 px
| ImageFileR1 = Ferrocene-from-xtal-3D-balls.png
| ImageSizeR1 = 80 px
(contracted; show full)
A second group at [[British Oxygen]] also unknowingly discovered ferrocene. Miller, Tebboth and Tremaine were trying to synthesise amines from hydrocarbons such as cyclopentadiene and ammonia in a modification of the [[Haber process]]. They published this result in 1952 although the actual work was done three years earlier.<ref
 name = Miller>{{cite journal| last1=Miller|first1= S. A.|last2=Tebboth|first2= J. A.|last3= Tremaine|first3= J. F.|journal= [[Journal of the Chemical Society|J. Chem. Soc.]]|year=1952| pages= 632–635| title=114. Dicyclopentadienyliron |doi=10.1039/JR9520000632}}</ref><ref name=r1>{{cite journal|first1= Pierre|last1= Laszlo|first2= Roald |last2=Hoffmann|title = Ferrocene: Ironclad History or Rashomon Tale? |journal = [[Angewandte Chemie|Angew. Chem. Int. Ed.]] |year = 2000 |volume = 39 |pages = 123–124 |do(contracted; show full)

==Synthesis and handling properties==
The first reported syntheses of ferrocene were nearly simultaneous.  Pauson and Kealy synthesised ferrocene using [[iron(III) chloride]] and a [[Grignard reaction|Grignard reagent]], cyclopentadienyl magnesium bromide.  Iron(III) chloride is suspended in [[anhydrous]] [[diethyl ether]] and added to the Grignard reagent, which is prepared by reacting [[cyclopentadiene]] with magnesium and [[bromoethane]] in anhydrous [[benzene]].<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|bibcode = 1951Natur.168.1039K }}</ref name = "Pauson_Kealy" />  An iron(III) salt was chosen as they sought to couple the cyclopentadienyl [[moiety (chemistry)|moieties]] to form dihydrofulvalene and then fullvalene, but ferrocene was formed instead as the oxidative formation of dihydrofulvalene also produced iron(II) by reduction, which in turn reacts with the Grignard.

:[[File:Kealy_Ferrocen_Synthese.svg|800px]]

[[File:Miller Ferrocen Synthese.svg|thumb|right|300px|The Miller ''et al.''<ref name = Miller /> approach to ferrocene]]
The other early synthesis of ferrocene was by Miller ''et al.'',<ref name = Miller>{{cite journal|journal = J. Chem. Soc.|last1 = Miller|first1 = S. A.|first2 = J. A.|last2 = Tebboth|first3 = J. F.|last3 = Tremaine|title = Dicyclopentadienyliron|year = 1952|volume = |page = 632–635|doi = 10.1039/JR9520000632}}</ref /> who reacted metallic iron directly with [[gas]]-phase cyclopentadiene at elevated temperature.<ref>{{cite journal|doi=10.1021/ja01636a080|title=Bis-cyclopentadienyl Compounds of Nickel and Cobalt|year=1954|last1=Wilkinson|first1=G.|authorlink1=Geoffrey Wilkinson|last2=Pauson|first2=P. L.|last3=Cotton|first3=F. A.|authorlink3=F. Albert Cotton|journal=[[J. Am. Chem. Soc.]]|volume=76|pages=1970|issue=7}}</ref>  An approach using [[iron pentacarbonyl]] was also reported.<ref>{{cite journa(contracted; show full)
{{Authority control}}

[[Category:Organoiron compounds]]
[[Category:Metallocenes]]
[[Category:Antiknock agents]]
[[Category:Sandwich compounds]]
[[Category:Cyclopentadienyl complexes]]