ON THE CHEMICAL NATURE OF 10-DICYANOMETHYLENE-ANTHRONE HYDRAZONE

The chemical nature of 10-dicyanomethylene-9-anthrone hydrazone was ex amined. It was shown that this compound bearing the conjugated ylidene malononitrile fragment and hydrazonic moiety did not undergo transform ations characteristic of ylidenemalonitriles, e.g., reduction and Mich ael addition, but possesses properties typical for hydrazones. Thus it could be hydrolyzed, acetylated, oxidized to yield the diazo compound , and reacted with acetone to form the corresponding azine. These prop erties were interpreted using semiempirical (AM1) and force field calc ulations.