Synthetic Reactions by Complex Catalysts. XXIV. A New Catalyst of Copper-Isocyanide Complex for the Michael Addition

It has been found that some binary systems of a copper compound (or metallic compounds) and an isocyanide catalyze the Michael addition reaction. As the copper component, Cu2O, metallic copper and copper acetylacetonate are effectual, whereas CuCl, CuCl2, and CuO are ineffectual. The catalyst of copper isocyanide complex is characterized by the selective activation of cyano olefin compounds such as acrylonitrile. This was demonstrated by the competitive addition of an active hydrogen compound to acrylonitrile and methyl acrylate. Some results of kinetics and spectroscopic studies have been explained by assuming a scheme involving coordination of olefin onto copper-isocyanide complex.