Reactions of Trimethylsilylmethyl Azide with Aromatic Acid Derivatives Catalyzed by Fluoride Ion.

The treatment of an aromatic acid halide with trimethylsilylmethyl azide (TMSMA) in the presence of potassium fluoride and crown ether gave triazine, methanediamine, and benzamide derivatives, while the reaction of acid anhydride with TMSMA gave tertiary amine together with methanediamine and benzamide under similar conditions.