Ferrocenecarbothioamide and N-ethoxycarbonylferrocenecarbothioamide: Synthesis, structure and application in synthesis of 2,4-diferrocenylthiazole

Ferrocenecarbothioamide (1) and its N-ethoxycarbonyl derivative (2) were synthesised by a Friedel–Crafts type reaction of ferrocene with potassium thiocyanate and ethoxycarbonyl isothiocyanate, respectively, in a strongly acidic medium. The X-ray structure of 1 was determined and shows conjugation between the ferrocene moiety and the thioamido group. Compound 1 reacts with chloroacetylferrocene affording 2,4-diferrocenylthiazole, whose structure was determined by X-ray diffraction and electronic properties studied by cyclic voltammetry.

Graphical abstractThe complexes 1 and 2 were synthesized by a Friedel–Crafts type reaction of ferrocene with potassium thiocyanide and ethoxycarbonyl isothiocyanate. 1 reacts with chloroacetylferrocene to afford 3. X-ray structures of 1 and 3 were determined. Redox properties of 3 were studied by means of cyclic voltammetry.Figure optionsDownload full-size imageDownload as PowerPoint slide