Pyridine N-alkylation by lithium, magnesium, and zinc alkyl reagents: Synthetic, structural, and mechanistic studies on the bis(imino)pyridine system

A detailed investigation of the MeLi reaction is conducted along with related reactions of bis(imino)pyridines with magnesium dialkyl and zinc dialkyl reagents. The synthetic, structural, and mechanistic investigation that examines the site selectivity of the alkylation, the reversibility of the process, the structures of key alkylation products, and the mechanism by which the alkylation process occurs, is described.