Reaction of bis(trimethylsilyl)acetonitrile, (trimethylgermyl)(trimethylsilyl)acetonitrile, and bis(trimethylgermyl)acetonitrile anions with aldehydes

Article abstract of DOI:10.1021/om00137a023

For a comparison of the chemical behavior of organosilicon and organogermanium compounds, bis-(trimethylsilyl)acetonitrile (3), (trimethylgermyl)(trimethylsilyl)acetonitrile (4), and bis(trimethyl-germyl)acetonitrile (5) were synthesized, and a Peterson type reaction was performed with them and a variety of aldehydes (12). High yields of 2-(trimethylsilyl)-2-alkenenitriles (15) from 3 and 2-(trimethylgermyl)-2-alkenenitriles (20) from 4 and 5 were obtained. High stereoselectivity giving E isomers was observed in the reaction of 3 and 5. The key intermediate in the reaction is also discussed.