On the Chemical Nature of 10-Dicyanomethyleneanthrone Hydrazone

Article abstract of DOI:10.1007/BF00811520

The chemical nature of 10-dicyanomethylene-9-anthrone hydrazone was examined.It was shown that this compound bearing the conjugated ylidenemalononitrile fragment and hydrazonic moiety did not undergo transformations characteristic of ylidenemalononitriles, e.g., reduction and Michael 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 properties were interpreted using semiempirical (AM1) and force field calculations. - Keywords. 10-Dicyanomethylene-9-anthrone hydrazone; 10-Dicyanomethylene-9-anthrone; N-Acetyl-10-dicyanomethylene-9-anthrone hydrazone; (10-dicyanomethylene-9,10-dihydroanthracene-9-ylidene)-isopropylidene-hydrazine; 9-Diazo-10-(dicyanomethylene)-9,10-dihydro anthracene; Acetylation; Oxidation; Hydrolysis; Semiempirical calculations.