Selectivity in the N- and/or C-Alkylation of Schiff Bases Catalyzed by Crown Ether

Article abstract of DOI:10.1246/bcsj.54.1273

The reaction of anions derived from Schiff bases (N-(α-methylbenzylidene)aniline and N-cyclohexylideneaniline) with ethyl iodide or diethyl sulfate in aprotic solvents, in the presence of 18-crown-6, is found to give a high ratio of N/(N+C) or C/(N+C) alkylation when conducted in benzene or in dioxane.