Synthesis and structure of silyl acetonitriles

An efficient route for the preparation of Mes2HSiCH2CN (1) and (Mes2HSi)2CHCN (2) is reported (Mes = 2,4,6-trimethylphenyl). Although the X-ray analyses for 1 and 2 reveal the CHnCN functionality (n = 1, 2) to be shielded by the Mes2HSi group, hydrolysis under basic conditions gave exclusively Mes2HSiOH (3), as a result of hydroxide-induced Si–C bond cleavage. In the solid state 3 is a tetramer forming an eight membered ring by H-bond interactions.

The new silyl acetonitriles Mes2HSiCH2CN (1) and (Mes2HSi)2CHCN (2) and the silanol Mes2SiHOH (3) have been derived from reactions of Mes2SiHCl with LiCH2CN (Mes = 2,4,6-trimethylphenyl). The X-ray structures of 1–3 are reported.Figure optionsDownload as PowerPoint slide