1,1'-Dilithioferrocene


1,1'-Dilithioferrocene is the organoiron compound with the formula Fe2. 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.

Synthesis and reactions

Treatment of ferrocene with butyl lithium gives 1,1'-dilithioferrocene, regardless of the stoichiometry. Typically the lithiation reaction is conducted in the presence of tetramethylethylenediamine. The adduct 32 has been crystallized from such solutions. Recrystallization of this adduct from thf gives 36.
1,1'-Dilithioferrocene reacts with a variety of electrophiles to afford disubstituted derivatives of ferrocene. These electrophiles include S8, chlorophosphines, and chlorosilanes.
The diphosphine ligand 1,1'-bis(diphenylphosphino)ferrocene 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.