New ferrocene containing 3-(arylthio)propan-1-ones: Synthesis, spectral characterization and crystal structure of 3-[(4-chlorophenyl)thio]-1-ferrocenylpropan-1-one, 3-[(4-chlorophenyl)thio]-1-ferrocenyl-3-phenylpropan-1-one and 3-[(4-chlorophenyl)thio]-3-

Three series of ferrocene containing 3-(arylthio)propan-1-ones (each of eight examples) have been synthesized by thia-Michael addition of the corresponding thiophenols to acryloylferrocene, 1-ferrocenyl-3-phenylprop-2-en-1-one and 3-ferrocenyl-1-phenylprop-2-en-1-one promoted by the catalyst generated from a sacrificial zirconium anode. All the newly synthesized compounds (16 in total) were characterized by spectral data, whereas single crystal X-ray structure analysis was performed for 3-[(4-chlorophenyl)thio]-1-ferrocenylpropan-1-one (1h), 3-[(4-chlorophenyl)thio]-1-ferrocenyl-3-phenylpropan-1-one (2h) and 3-[(4-chlorophenyl)thio]-3-ferrocenyl-1-phenylpropan-1-one (3h). Molecular geometry and structural characteristics of three thiaketones (1h, 2h and 3h) were analysed and compared in detail. It was found that all three molecules do not form classical H-bonds and π⋯π interactions (regardless of the presence of 3 or 4 aromatic rings per a molecule). However, all three crystal structures abound in intermolecular C–H⋯π interactions while 2h and 3h in addition form intramolecular C–H⋯π as only evident interaction within the molecules.

Graphical abstractThree series of ferrocene containing 3-(arylthio)propan-1-ones (24 in total, 16 being new ones) have been synthesized by thia-Michael addition of 8 thiophenols to the corresponding enones promoted by the catalyst generated from a sacrificial zirconium anode. The single crystal X-ray structure analysis was performed for three of the synthesized compounds.Figure optionsDownload full-size imageDownload as PowerPoint slide