Beyond Acetylferrocene: The Synthesis and NMR Spectra of a Series of Alkanoylferrocene Derivatives

This experiment offers a new twist to a popular undergraduate synthesis laboratorythe conversion of ferrocene to acetylferrocene. The goal of this experiment is to prepare a series of nine alkanoylferrocene complexes that yield more thought-provoking and challenging NMR spectra than that obtained for acetylferrocene. If these complexes are described as alkyl ferrocenyl ketones, the alkyl groups range from methyl (1), ethyl (2), n-propyl (3), isopropyl (4), n-butyl (5), isobutyl (6), tert-butyl (7), n-pentyl (8), to n-heptyl (9). The synthesis and isolation of these crude complexes are achieved by using acid anhydrides or acyl chlorides. In the second week, the crude product was purified by column chromatography and dried. In the third week, 1H and 13C NMR were obtained in CDCl3. These spectra are presented and discussed.