Ferrocene is an organometallic compound that readily undergoes oxidation in atmosphere under acidic conditions. However, because of its diamagnetic nature, ferrocene does not lend itself to structural analysis by nuclear magnetic resonance (NMR) spectroscopy. In this work, the oxidation of ferrocene and several of its derivatives were analyzed by liquid chromatography-mass spectrometry (LC-MS). An electrospray ionization (ESI) source was used, with picrate serving as the counter ion. This method is particularly effective for studying oxidation of ferrocenes because their reactivity toward oxygen under ambient conditions is low.
References
[1]
Curphey, T.J., Santor, J.O., Rosenblum, M. and Kinchards, J.H. (1960) Protonation of Metallocenes by Strong Acids. Structure of the Cation. Journal of the American Chemical Society, 82, 5249-5250. https://doi.org/10.1021/ja01504a062
[2]
Bromly Aly, M.R., Upadhyay, J., Wasserman, A. and Woolliams, P.R. (1965) Paramagnetic Ferrocene Acid Adducts. Kinetics of Electron Transfer to Proton Acids. Chemical Communications, 0, 404-406.
[3]
Bitterwolf, T.E. and Ling, A.C. (1972) Metallocene Basicity. II. Reaction of the Ferrocenonium Cation with Molecular Oxygen and Sulfur Dioxide. Journal of Organometallic Chemistry, 40, C29-C32.
https://doi.org/10.1016/S0022-328X(00)86974-0
[4]
Broadhead, G.D. and Pauson, P.L. (1955) Ferrocene Derivatives. II. Arylation. Journal of the Chemical Society, 0, 367-370. https://doi.org/10.1039/jr9550000367
[5]
Rausch, M., Vogel, M.V. and Rosenberg, H. (1957) Derivatives of Ferrocene. II. Some reduction Products of Benzoylferrocene and 1,1’-Dibenzoylferrocene. Journal of Organic Chemistry, 22, 903-906. https://doi.org/10.1021/jo01359a012