779339-32-1Relevant articles and documents
Ferrocenecarboselenoic acid: Synthesis and some reactions
Takahashi, Toshinori,Niyomura, Osamu,Kato, Shinzi,Ebihara, Masahiro
, p. 108 - 114 (2013/03/28)
The first ferrocenecarboselenoic acid was synthesized and characterized. The existence of tautomeric equilibrium between the selenol (FcCOSeH) and selenoxo forms (FcCSeOH) in polar solvents was proven by 1H-, 13C- and 77Se-NMR spectra. The selenoxo form exists predominantly in a polar solvent at low temperature below -70 °C. Treatment of this acid with lithium, sodium, and potassium hydrides and with rubidium and cesium fluorides gave the corresponding alkali metal ferrocenecarboselenoates in quantitative yields. Treatment with 4-methylphenyl isocyanate at room temperature led to ferrocenoyl 4-methylphenylcarbamoyl selenide FcCOSeC(O)NHC6H4Me-4 in high yield. A similar reaction with phenyl isothiocyanate formed a mixture of FcCOSeC(S)NHPh and FcCOSeC(SH)=NPh in moderate to good yield. The carboselenoic acid readily reacted with piperidine to give piperidinium ferrocenecarboselenoate in good yield. Air oxidation of this selenoic acid afforded diferrocenoyl selenide as a major product along with diferrocenoyl diselenide. The structures of the selenide (FcCO)2Se and diselenide (FcCOSe)2 were examined by single-crystal X-ray analysis. Copyright