[(α‐Cyanobenzyllithium. Tetramethylethylenediamine)₂. Benzene]: X‐ray Structure Analysis of an α‐Nitrile “Carbanion”

Abstract

A “ketene iminate” and not a carbanion is present in the title compound 1·C6H6. The bond lengths in the CCN group deviate considerably from those in ketene imines such as 2. In comparison, enolates have practically the same bond lengths as enol ethers. This difference is due to the different stabilization of a negative charge by nitriles and carbonyl compounds.