Bis(eta-cyclopentadienyl) iron → N,N,N',N'-Tetramethylethylenediamine

HRID 565133Notes

Reaction equation

HRID 565133 reaction equation
[Li].[Li].[CH-:3]1[CH:7]=[CH:6][CH:5]=[CH:4]1.[CH-:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1.[Fe+2:13].[CH3:14][N:15]([CH3:21])[CH2:16][CH2:17][N:18]([CH3:20])[CH3:19].C([Li:26])CCC.[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2]>CCCCCC>[Li:26][C-:3]1[CH:7]=[CH:6][CH:5]=[CH:4]1.[C-:8]1([Li:26])[CH:12]=[CH:11][CH:10]=[CH:9]1.[Fe+2:13].[CH3:14][N:15]([CH3:21])[CH2:16][CH2:17][N:18]([CH3:20])[CH3:19]

Participants

7

Reactant 4

HCID 7611Bis(eta-cyclopentadienyl) ironHCID 8037N,N,N',N'-Tetramethylethylenediamine2×HCID 131722255HCID 131722255, compoundHCID 178418339Butyllithium

Product 2

HCID 8037N,N,N',N'-TetramethylethylenediamineYield 66%HCID 178506419HCID 178506419, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent3×

Procedure

During a first step, ferrocene dilithium complexed with tetramethylethylenediamine (TMEDA) was prepared: In a glove box under argon, there is added 37 ml of freshly distilled TMEDA (247 mmoles) and 40 ml of anhydrous hexane in a 1 1 flask. There is then added drop wise 154 ml of a 1.6 M solution of butyllithium in hexane (247 mmoles, commercially available from Aldrich). After 10 min, there is added drop wise 18.6 g of ferrocene (100 mmoles) in solution in 500 ml of anhydrous hexane while keeping a strong stirring of the solution. After one night, orange crystals appeared in the solution, which were recovered by filtering the solution on a fritted glass of porosity No 4. After drying under vacuum, there is obtained 28.4 g of 1,1′-dilithio-ferrocene&Circlesolid;2 TMEDA (66% yield) which was preserved under argon.

Workup

  1. customwas prepared
  2. waitAfter one night
  3. customwere recovered
  4. filtrationby filtering the solution on a fritted glass of porosity No 4
  5. customAfter drying under vacuum

Sources & evidence

ORD record
ord-cc4f8b19ad814a6d98864a9ac7b63c23
Source dataset
uspto-grants-2001_01
Patent number
US06171522B2

Reaction notes

Loading…