[tert‐Butylcyanide · Lithium Bis(trimethylsilyl)amide]₂, a Model of the Intermediate RCN. MR′ Complex Formed in Reactions of Cyanides RCN with Organometallic Compounds R′M

The dialkylation and dideuteration of cyanides are proposed to proceed through intermediates of the type RR′CHCN · LiR″. The title compound 1 (central framework shown on the right) is the first structurally characterized compound of this type. The results of ab initio calculations on the model compound H₃CCN · LiNH₂ are in agreement with the high stability and the energetically favorable intramolecular proton shift found experimentally. (Figure Presented.)