Chemistry:Cyclopentadienyliron dicarbonyl methyl
2Me.svg)
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| Names | |
|---|---|
| Other names
FpMe
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| 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). | |
| Infobox references | |
Cyclopentadienyliron dicarbonyl methyl is an organoiron complex with the formula (C
5H
5)Fe(CO)
2CH
3. 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 (C
5H
5)Fe(CO)(PR
3)CH
3. When heated with phosphine ligands, the chiral acetyl complex (C
5H
5)Fe(CO)(PR
3)COCH
3 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 + HSiR
3 → R
3SiCN + R'SiR
3
References
- ↑ R. Bruce King (1965). Organometallic Syntheses. 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.
- ↑ 4.0 4.1 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.
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