Acid-catalyzed self-alkylation of FcCH2NHPh. Solid-state structures of FcCH2NHPh and (FcCH2)NPh

N-(ferrocenylmethyl)aniline (2) readily undergoes an acid-catalyzed self-alkylation to give a mixture of N,N-bis(ferrocenylmethyl)aniline (3) and aniline. In the alkylation reaction, amine 2 acts as the alkylated nucleophile as well as a source of the alkylating species, the ferrocenylmethylium cation, after protonation. Solid-state structures of amines 2 and 3 were determined by X-ray diffraction.