New ferrocenyl amine derivatives: N-silyl, N-stannyl and N-boryl ferrocenyl amines

N-Ferrocenyl amine, Fc-NH2 (1), reacts with chlorosilanes in the presence of Et3N to give N-silylated derivatives such as Fc-NH-SiMe3 (2), Fc-NH-SiMe2H (3) and (Fc-NH)2SiMe2 (6). N-Lithiation of 1, followed by reaction with Me3SnCl, gives Fc-NH-SnMe3 (4) which is in equilibrium with Fc-N(SnMe3)2 (5). Lithiated 1, Fc-NH-Li, reacts with Me2SnCl2 (1:1) to give the trimer (Fc-N-SnMe2)3 (7). The tin analogue of 6 was not found. Lithiation of 2, followed by reaction with Me3SnCl, affords Fc-N(SiMe3)-SnMe3 (8). The silylamine 2 reacts with the 9-borabicyclo[3.3.1]nonane dimer (H-9-BBN)2 and with tetraethyldiborane(6), either by elimination of H2 to give Fc-N(SiMe3)-(9-BBN) (9) and Fc-N(SiMe3)-BEt2 (10), or by elimination of Me3SiH to give Fc-NH-(9-BBN) (11) and Fc-NH-BEt2 (12), respectively, depending on the reaction conditions.