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

Abstract

N-Ferrocenyl amine, Fc-NH 2 ( 1), reacts with chlorosilanes in the presence of Et 3N to give N-silylated derivatives such as Fc-NH-SiMe 3 ( 2), Fc-NH-SiMe 2H ( 3) and (Fc-NH) 2SiMe 2 ( 6). N-Lithiation of 1, followed by reaction with Me 3SnCl, gives Fc-NH-SnMe 3 ( 4) which is in equilibrium with Fc- N(SnMe 3) 2 ( 5). Lithiated 1, Fc-NH-Li, reacts with Me 2SnCl 2 (1:1) to give the trimer (Fc- N-SnMe 2) 3 ( 7). The tin analogue of 6 was not found. Lithiation of 2, followed by reaction with Me 3SnCl, affords Fc- N(SiMe 3)-SnMe 3 ( 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 H 2 to give Fc- N(SiMe 3)-(9-BBN) ( 9) and Fc- N(SiMe 3)-BEt 2 ( 10), or by elimination of Me 3SiH to give Fc-NH-(9-BBN) ( 11) and Fc-NH-BEt 2 ( 12), respectively, depending on the reaction conditions.