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.
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IUPAC name
1,1'-Dilithioferrocene
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3D model (JSmol)
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PubChem CID
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Properties | |
C10H8FeLi2 | |
Molar mass | 197.90 g·mol−1 |
Appearance | orange solid |
Hazards | |
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Main hazards
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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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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.
The reaction of ferrocene with one equivalent of butyllithium mainly affords dilithioferrocene. Monolithioferrocene can be obtained using tert-butyllithium.[4]