METAL-CATALYZED CARBON-CARBON BOND FORMATION IN THE REACTION OF MALONONITRILE WITH BETA-DICARBONYLS

Nickel acetylacetonate effectively catalyses the carbon-carbon bond fo rmation between malononitrile and beta-dicarbonyls. In these metal-cat alysed reactions malononitrile behaves as an electrophile towards the intercarbonylic carbon, so exhibiting a reverse reactivity compared wi th that one under basic or thermal conditions. The resulting organic p roducts are beta-cyanomethylene-beta-enamino dicarbonyls (2a-h), which are obtained in good-to fair yield. beta-Iminodicarbonyl complexes of nickel(II) and copper(II), which are likely intermediates in the cata lytic cycle, are synthesised by reaction of the metal beta-carbonyleno late with malononitrile or of the metal acetate with the catalysis pro duct (2a, d).