Abstract
RuCl 2(PPh 3) 3 catalyzed condensation of 1,1′-ferrocenedimethanol with primary amines afforded N-alkyl- or N-aryl-2-aza-[3]-ferrocenophanes which were characterized by 1H and 13C NMR spectra. X-ray crystallography of N-(4-butylphenyl)-2-aza-[3]-ferrocenophane unequivocally revealed its mononuclear structure. The N–C (aryl) bond distance is shorter than the N–CH 2 single bond due to extension of π-conjugation of the aromatic ring to the nitrogen atom. N-Hexyl-2-aza-[3]-ferrocenophane reacts with methyl iodide to give the N-methylated product which was characterized by NMR spectroscopy and X-ray crystallography. N-Aryl-2-aza-[3]-ferrocenophanes exhibited reversible redox between ferrocene and ferrocenium cations and an irreversible oxidation peak at a higher oxidation potential.
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