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ChemicalBook CAS DataBase List Ferrocene
102-54-5

Ferrocene synthesis

5synthesis methods
Dicyclopentadienyliron may be obtained in a single-step synthetic route by heating cyclopentadiene with iron or iron pentacarbonyl at 300°C:
2C5H5 + Fe → (C5H5)2Fe
Also, it can be prepared by the reaction of iron(II) chloride with cyclopentadiene in the presence of an alkyl amine or a similar base.
Another convenient method of preparing this π-complex of iron is a twostep process in which the first step involves preparation of cyclopentadienyl Grignard reagent, such as 2,4-cyclopentadienylmagnesium bromide C5H5MgBr which may then be combined with ferric chloride to yield dicyclopentadienyl iron:
3C5H5MgBr + FeCl3 → (C5H5)2Fe + 3MgBrCl
Another general method of preparation involves the reaction of cyclopentadiene with sodium metal or sodium hydride in tetrahydrofuran (THF). Addition of iron(II) chloride to this solution forms the complex dicyclopentadienyliron:
2C5H6 + 2Na → 2C5H5ˉ + 2Na+ + H2
In 3:2 molar ratio of cyclopentadiene to sodium cyclopentene is obtained along with cyclopentadienidide (C5H5ˉ ) anion:
3C5H6 + 2Na → 2C5H5¯ + 2Na+ + C5H8
FeCl2 + 2C5H6Na → (C5H5)2Fe + 2NaCl
-

Yield:102-54-5 85%

Reaction Conditions:

with diethylamine in 1,2-dimethoxyethane;diethylamine;amine method; FeCl3:C5H6=1.3;;

References:

Pruett, R. L.;Morehouse, E. L. [Advances in Chemistry Series,1959,vol. 23,p. 368 - 371] [Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Fe: Org.Verb.A1, 2.1.1.2, page 16 - 18]

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