1,1'-Dilithioferrocene
Chemical compound
From Wikipedia, the free encyclopedia
1,1'-Dilithioferrocene is the organoiron compound with the formula Fe(C5H4Li)2. It is exclusively generated and isolated as a solvate, using either ether or tertiary amine ligands bound to the lithium centers. Regardless of the solvate, dilithioferrocene is used commonly to prepare derivatives of ferrocene.[1]
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| Names | |
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| IUPAC name
1,1'-Dilithioferrocene | |
| Identifiers | |
3D model (JSmol) |
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PubChem CID |
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| Properties | |
| C10H8FeLi2 | |
| Molar mass | 197.90 g·molâ1 |
| Appearance | orange solid |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards |
pyrophoric |
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 and reactions
Treatment of ferrocene with butyl lithium gives 1,1'-dilithioferrocene, regardless of the stoichiometry (monolithioferrocene requires special conditions for its preparation). Typically the lithiation reaction is conducted in the presence of tetramethylethylenediamine (tmeda). The adduct [Fe(C5H4Li)2]3(tmeda)2 has been crystallized from such solutions.[1] Recrystallization of this adduct from thf gives [Fe(C5H4Li)2]3(thf)6.[2]
1,1'-Dilithioferrocene reacts with a variety of electrophiles to afford disubstituted derivatives of ferrocene. These electrophiles include S8 (to give 1,1'-ferrocenetrisulfide), chlorophosphines, and chlorosilanes.[3]
The diphosphine ligand 1,1'-bis(diphenylphosphino)ferrocene (dppf) is prepared by treating dilithioferrocene with chlorodiphenylphosphine.
Monolithioferrocene
The reaction of ferrocene with one equivalent of butyllithium mainly affords dilithioferrocene. Monolithioferrocene can be obtained using tert-butyllithium.[4]