Cyclopentadienyliron dicarbonyl methyl

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]

Cyclopentadienyliron dicarbonyl methyl

Names
Other names FpMe
Identifiers
CAS Number	12080-06-7
3D model (JSmol)	Interactive image
InChI InChI=1S/C5H5.2CO.CH3.Fe/c1-2-4-5-3-1;2*1-2;;/h1-5H;;;1H3;/q-1;;;;+1 Key: GLKDETLONPSPJC-UHFFFAOYSA-N
SMILES [CH-]1C=CC=C1.C[Fe+]([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

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