Decamethyl ferrocene

Structural formula
General
Surname	Decamethyl ferrocene
other names	Bis (pentamethylcyclopentadienyl) iron (II)
Molecular formula	C 20 H 30 Fe
Brief description	orange odorless solid
External identifiers / databases
EC number	601-765-9
ECHA InfoCard	100.116.086
PubChem	11984658
Wikidata	Q5248735
properties
Molar mass	326.30 g mol −1
Physical state	firmly
Melting point	277 ° C (decomposition)
solubility	almost insoluble in water
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-280-305 + 351 + 338-304 + 340-405-501
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Decamethylferrocene is a chemical compound of iron from the group of sandwich complexes or metallocenes .

Extraction and presentation

Decamethylferrocene can be obtained from a derivative of pentamethylcyclopentadiene by reaction with iron (II) chloride .

{\ displaystyle \ mathrm {2 \ Li (C_ {5} Me_ {5}) + FeCl_ {2} \ longrightarrow Fe (C_ {5} Me_ {5}) _ {2} +2 \ LiCl}}

properties

Decamethylferrocene is an orange crystalline odorless solid.

use

Decamethylferrocene is used in the production of charge transfer complexes . With mild oxidizing agents such as Ag ⁺ , decamethylferrocene Cp * ₂ Fe (with Cp * = pentamethylcyclopentadienyl) is oxidized to the green monocation Cp * ₂ Fe ⁺ (paramagnetic, an unpaired electron). With very strong oxidizing agents like SbF ₅ or AsF ₅ in SO ₂ or XeF ⁺ Sb ₂ F ₁₁^- in HF / SbF ₅ , the oxidation to the brown dication succeeds (paramagnetic, two unpaired electrons). Depending on the choice of the weakly coordinating counterion, Cp * ₂ Fe ^{2+ has} parallel Cp * rings (for Sb ₂ F ₁₁^- ) or a kink angle of 17 ° between the Cp * rings (for SbF ₆^- ).

Individual evidence

↑ ^a ^b ^c ^d ^e Data sheet Decamethylferrocenes, 99% from AlfaAesar, accessed on June 27, 2015 ( PDF )(JavaScript required) .
↑ ^a ^b Data sheet bis (pentamethylcyclopentadienyl) iron (II), 97% from Sigma-Aldrich , accessed on June 27, 2015 ( PDF ).
↑ RB King, MB Bisnette: Organometallic chemistry of the transition metals XXI. Some π-pentamethylcyclopentadienyl derivatives of various transition metals. In: Journal of Organometallic Chemistry. 8, 1967, p. 287, doi : 10.1016 / S0022-328X (00) 91042-8 .
^ Antonio Togni: Ferrocenes Homogeneous Catalysis, Organic Synthesis, Materials Science . John Wiley & Sons, 2008, ISBN 3-527-61558-X , pp. 440 ( limited preview in Google Book Search).
↑ M. Malischewski, M. Adelhardt, J. Sutter, K. Meyer, K. Seppelt: Isolation and structural and electronic characterization of salts of the decamethylferrocene dication . In: Science . tape 353 , no. 6300 , August 12, 2016, ISSN 0036-8075 , p. 678-682 , doi : 10.1126 / science.aaf6362 , PMID 27516596 ( sciencemag.org [accessed December 3, 2016]).

[Alfa-1] Data sheet Decamethylferrocenes, 99% from AlfaAesar, accessed on June 27, 2015 ( PDF )(JavaScript required) .

[Sigma-2] Data sheet bis (pentamethylcyclopentadienyl) iron (II), 97% from Sigma-Aldrich , accessed on June 27, 2015 ( PDF ).

[DOI10.1016/S0022-328X(00)91042-8-3] RB King, MB Bisnette: Organometallic chemistry of the transition metals XXI. Some π-pentamethylcyclopentadienyl derivatives of various transition metals. In: Journal of Organometallic Chemistry. 8, 1967, p. 287, doi : 10.1016 / S0022-328X (00) 91042-8 .

[Antonio_Togni-4] Antonio Togni: Ferrocenes Homogeneous Catalysis, Organic Synthesis, Materials Science . John Wiley & Sons, 2008, ISBN 3-527-61558-X , pp. 440 ( limited preview in Google Book Search).

[5] M. Malischewski, M. Adelhardt, J. Sutter, K. Meyer, K. Seppelt: Isolation and structural and electronic characterization of salts of the decamethylferrocene dication . In: Science . tape 353 , no. 6300 , August 12, 2016, ISSN 0036-8075 , p. 678-682 , doi : 10.1126 / science.aaf6362 , PMID 27516596 ( sciencemag.org [accessed December 3, 2016]).