ORGANOMETALLOIDAL DERIVATIVES OF THE TRANSITION-METALS .33. REACTIONSOF FERROCENYLCARBOXALDEHYDE WITH BASE AND TRIMETHYLSILYLCYANIDE - A NEW HIGH-YIELD REACTION FOR THE FORMATION OF CYANO-AMINES OR SILYLETHERS

Treatment of ferrocenecarboxaldehyde with base at 0-degrees-C, lithium diisopropylamide (LDA) or n-butyllithium, followed by the addition of trimethylsilylcyanide, produced 1-(diisopropylamino)cyanomethylferroc ene, FcCH(N{iPr}2)(CN) (II) or 1-trimethylsiloxy-n-pentylferrocene, Fc CH(nBu)OSiMe3 (IIIa). The reaction of naphthaldehyde, NpCHO, with LDA/ Me3SiCN led to formation of 1-(diisopropylamino)cyanomethylnaphthalene , NpCH{N(iPr)2}(CN) suggesting a general new synthesis for cyanoamines . The reaction of ferrocenecarboxaldehyde with Me3SiCN led to the expe cted silylether FcCH(CN)OSiMe3 (I). An alternative synthesis of ferroc enylmethylsilylethers, FcCH2OSiR3 (IV), involved the reaction of 1-fer rocenylmethanol with R3SiCl in the presence of pyridine. The basicity of the new silylethers III and IV is reported.