Organometalloidal derivatives of the transition metals: XXXIII. Reactions of ferrocenylcarboxaldehyde with base and trimethylsilylcyanide. A new high yield reaction for the formation of cyano-amines or silylethers☆

Abstract Treatment of ferrocenecarboxaldehyde with base at 0°C, lithium diisopropylamide (LDA) or n-butyllithium, followed by the addition of trimethylsilylcyanide, produced 1-(diisopropylamino)cyanomethylferrocene, FcCH(N{ i Pr} 2 (CN) ( II ) or 1-trimethyl-siloxy-n-pentylferrocene, FcCH( n Bu)OSiMe 3 ( IIIa ). The reaction of naphthaldehyde, NpCHO, with LDA/Me 3 SiCN led to formation of 1-(diisopropylamino)cyanomethylnaphthalene, NpCH{N( i Pr) 2 }(CN) suggesting a general new synthesis for cyanoamines. The reaction of ferrocenecarboxaldehyde with Me 3 SiCN led to the expected silylether FcCH(CN)OSiMe 3 ( I ). An alternative synthesis of ferrocenylmethylsilylethers, FcCH 2 OSiR 3 ( IV ), involved the reaction of 1-ferrocenylmethanol with R 3 SiCl in the presence of pyridine. The basicity of the new silylethers III and IV is reported.