1,1'-Dilithioferrocene

FcLi2.svg 110 px 1,1'-Dilithioferrocene 33272-09-2 correct CAS 9238543 11063390 1S/2C5H4.Fe.2Li/c2*1-2-4-5-3-1;;;/h2*1-4H;;;/q2*-1;;2*+1 CWUATGTYNYDRDF-UHFFFAOYSA-N [Li+].[Li+].[CH]1[CH][CH][C-][CH]1.[CH]1[CH][CH][C-][CH]1.[Fe] 10 8 1 2 orange solid pyrophoric 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. 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.10.1021/om00131a023 The Structure of the 3:2 Adduct of 1,1'-Dilithioferrocene with Tetramethylethylenediamine 1985 Butler Ian R. Cullen William R. Ni Jijin Rettig Stephen J. Organometallics 4 12 2196–2201 Recrystallization of this adduct from thf gives [Fe(C5H4Li)2]3(thf)6.10.1021/om800765a Comparison of Doubly Lithiated, Magnesiated, and Zincated Ferrocenes: [Fe(η5-C5H4)2]2Zn2(tmeda)2, the First Example of a [1.1]Ferrocenophane with Bridging First-Row Transition Metal Atoms 2008 Perucha Alejandro Sánchez Heilmann-Brohl Julia Bolte Michael Lerner Hans-Wolfram Wagner Matthias Organometallics 27 23 6170–6177 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.David E. Herbert Ulrich F. J. Mayer Ian Manners Strained Metallocenophanes and Related Organometallic Rings Containing pi-Hydrocarbon Ligands and Transition-Metal Centers Angew. Chem. Int. Ed. 2007 46 5060–5081 10.1002/anie.200604409 17587203 27 380px|thumb|center|Some transformations of dilithioferrocene. 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.10.1016/S0022-328X(01)00743-4 Synthesis, Structural Characterization and 57Fe-Mössbauer Spectra of Ferrocenylhexasilanes 2001 Rautz Hermann Stüger Harald Kickelbick Guido Pietzsch Claus Journal of Organometallic Chemistry 627 2 167–178 References Category:Ferrocenes Category:Sandwich compounds Category:Cyclopentadienyl complexes Category:Organolithium compounds