Cyclopentadienyliron dicarbonyl methyl

Cyclopentadienyliron dicarbonyl methyl
Names
	Other names FpMe
Identifiers
CAS Number	12080-06-7;
3D model (JSmol)	Interactive image;
	SMILES [cH-]1cccc1.[CH3-][Fe+2]([C]=O)[C]=O;
Properties
Chemical formula	C8H5FeO2
Molar mass	188.971 g·mol−1
Appearance	orange wax
Melting point	72–82 °C (162–180 °F; 345–355 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Cyclopentadienyliron dicarbonyl methyl is an organoiron complex with the formula (C₅H₅)Fe(CO)₂CH₃. It is an orange volatile solid that is sensitive to air.^[1]

Synthesis

The compound arises from cyclopentadienyliron dicarbonyl dimer. Reduction of the latter give sodium cyclopentadienyl iron dicarbonyl, which can be alkylated.^[2]^[3]

Reactions

The compound was influential in the development of organometallic chemistry.^[4] Under the influence of UV radiation, one CO ligand can be replaced by phosphine ligands to give chiral derivatives (C₅H₅)Fe(CO)(PR₃)CH₃. When heated with phosphine ligands, the chiral acetyl complex (C₅H₅)Fe(CO)(PR₃)COCH₃ arises instead. Many reagents insert into the Fe-CH₃ bond including sulfur dioxide, tetracyanoethylene, and stannous chloride.^[4] The compound catalyzes the scission of nitriles:^[5]

R'CN + HSiR₃ → R₃SiCN + R'SiR₃

References

^ R. Bruce King (1965). Organometallic Syntheses. Vol. 1. New York: Academic Press. p. 151.
^ Green, James R. (2001). "Sodium Dicarbonylcyclopentadienylferrate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289x.rs060. ISBN 0-471-93623-5.
^ Piper, T.S.; Wilkinson, G. (1956). "Alkyl and aryl derivatives of π-cyclopentadienyl compounds of chromium, molybdenum, tungsten, and iron". Journal of Inorganic and Nuclear Chemistry. 3 (2): 104–124. doi:10.1016/0022-1902(56)80073-0.
^ ^a ^b Pannell, Keith H.; Sharma, Hemant K. (2010). "(Cyclopentadienyl)dicarbonylmethyliron ((η⁵-C₅H₅)Fe(CO)₂CH₃, FpMe), a Seminal Transition-Metal Alkyl Complex: Mobility of the Methyl Group". Organometallics. 29 (21): 4741–4745. doi:10.1021/om1004594.
^ Nakazawa, Hiroshi; Itazaki, Masumi; Kamata, Kouji; Ueda, Kensuke (2007). "Iron-Complex-Catalyzed C—C Bond Cleavage of Organonitriles: Catalytic Metathesis Reaction between H—Si and R—CN Bonds to Afford R—H and Si—CN Bonds". Chemistry: An Asian Journal. 2 (7): 882–888. doi:10.1002/asia.200700076. PMID 17534995.

[1] R. Bruce King (1965). Organometallic Syntheses. Vol. 1. New York: Academic Press. p. 151.

[2] Green, James R. (2001). "Sodium Dicarbonylcyclopentadienylferrate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289x.rs060. ISBN 0-471-93623-5.

[3] Piper, T.S.; Wilkinson, G. (1956). "Alkyl and aryl derivatives of π-cyclopentadienyl compounds of chromium, molybdenum, tungsten, and iron". Journal of Inorganic and Nuclear Chemistry. 3 (2): 104–124. doi:10.1016/0022-1902(56)80073-0.

[Pannell-4] Pannell, Keith H.; Sharma, Hemant K. (2010). "(Cyclopentadienyl)dicarbonylmethyliron ((η⁵-C₅H₅)Fe(CO)₂CH₃, FpMe), a Seminal Transition-Metal Alkyl Complex: Mobility of the Methyl Group". Organometallics. 29 (21): 4741–4745. doi:10.1021/om1004594.

[5] Nakazawa, Hiroshi; Itazaki, Masumi; Kamata, Kouji; Ueda, Kensuke (2007). "Iron-Complex-Catalyzed C—C Bond Cleavage of Organonitriles: Catalytic Metathesis Reaction between H—Si and R—CN Bonds to Afford R—H and Si—CN Bonds". Chemistry: An Asian Journal. 2 (7): 882–888. doi:10.1002/asia.200700076. PMID 17534995.

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