Uses
1,1'-Ferrocenedicarboxaldehyde is used as a starting material to prepare 1'-formyl-ferrocenecarboxylic acid and 1'-[(E)-3-oxo-but-1-enyl]-ferrocenecarboxylic acid by oxidation with potassium permanganate using water/acetonitrile mixture and water/acetone mixture respectively.
Synthesis
The general procedure for the synthesis of 1,1'-ferrocenedicarboxaldehyde from ferrocene and N,N-dimethylformamide, based on a modification of the literature procedure [26b], was as follows: ferrocene (10 g, 0.054 mol) was dissolved in anhydrous hexanes (200 mL) at room temperature, n-butyllithium solution (67 mL, 1.6 M, 0.10 mol) was added slowly and dropwise, followed by the addition of tetramethylene methyl ethylenediamine (TMEDA) (14.7 g, 0.25 mol). It was shown that the addition of the reactants at -50 °C had no significant effect on the yield. After stirring the reaction mixture for 18 h at room temperature, the dilithiated ferrocene precipitated as an orange solid. The suspension was cooled to 0 °C, N,N-dimethylformamide (DMF) (7.85 g, 0.11 mol, 8.3 mL) was added and stirring was continued for 2 h at room temperature.
References
[1] Journal of Organometallic Chemistry, 1993, vol. 463, # 1-2, p. 163 - 168
[2] Journal of Organometallic Chemistry, 2013, vol. 740, p. 61 - 69
[3] Journal of Organometallic Chemistry, 2009, vol. 694, # 13, p. 2020 - 2028
[4] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 10, p. 1551 - 1557
[5] European Journal of Inorganic Chemistry, 2014, vol. 2014, # 36, p. 6212 - 6219
