Cyclopentadienyliron dicarbonyl methyl
2Me.svg) | |
| Names | |
|---|---|
| Other names
FpMe
| |
| Identifiers | |
| 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).
| |
Cyclopentadienyliron dicarbonyl methyl is an organoiron complex with the formula (C5H5)Fe(CO)2CH3. It is an orange volatile solid that is sensitve to air.[1] The compound arises from the methylation of sodium cyclopentadienyl iron dicarbonyl.[2][3]
Reactions
[edit]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
[edit]- ^ 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.