Cyclopentadienyliron dicarbonyl methyl
Chemical compound
From Wikipedia, the free encyclopedia
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]
2Me.svg) | |
| Names | |
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| Other names
FpMe | |
| Identifiers | |
3D model (JSmol) |
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| Properties | |
| 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).
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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