Synthesis And Characterization Of Two Series Of Aromatic Sec-Amines Bearing Ferrocenyl Group

Acylation of ferrocene by acetyl- or benzoyl chloride catalyzed by aluminum chloride produced the corresponding acylferrocenes. Condensation of the these two acylferrocenes wtih anilines, such as o-, m-, p-chloroanilines, p-methoxy, p-methyl and aniline gave the corresponding ketimines, respectively. Reduction of these imines with sodium borohydride in aqueous methanol or lithaium aluminum hydride in anhydrous THF or diethyl ether afforded sec-amines bearing ferrocenyl group. An attempt at synthesis of tert-amines from the sec-amines with the reagents e.g., sodium cyanoborohydride, formaldehyde, and acetic acid in acetylnitrile was unsucessful.This abnormal phenominon could be easily rationalized by the reduction of 1-ferrocenylethyl or benzyl cation resulted from the corresponding tert-amines. Six imines compounds were characterized by IR spectra. The structures of the sec-amines derived from acetylferrocene and anilines were identified by elemental analysis, IR and 1H NMR. Similarly, three imines and the subsquent sec-amines from benzoylferrocene and anilines were also confirmed by elemental analysis, IR and 1H NMR...