2,3-diferrocenyl-(1-triphenylphosphoranylidene)ketene: Synthesis and interactions with O, C, N, S, Se nucleophiles, characterization and X-ray diffraction

Abstract

The opening of the ring of 2,3-diferrocenylcyclopropenone 1 with triphenylphosphine was studied to obtain 2,3-diferrocenyl-(3-triphenylphosphoranylidene) ketene 3. This was subsequently electrophile activated to react with different nucleophiles (O, C, N, S, Se) to obtain α,β-unsaturated carbonyl compounds with a preferable selectivity (E), which were stable under environmental conditions. The reduction reaction of the double bond of the α,β-unsaturated carbonyl compound was studied in the presence of hydrogen iodide. The structures of the synthesized compounds were established on the basis of data obtained from ¹H and ¹³C NMR spectroscopy and further confirmed by X-ray diffraction analysis.