Oxidative C-O coupling of benzylmalononitrile with 3-(hydroxyimino)pentane-2,4-dione

Oxidative C-O coupling of benzylmalononitrile with 3-(hydroxyimino)pentane-2,4-dione has been accomplished. This reaction is the first example of oxidative C-O coupling of a malononitrile with an oxime. The best yield (65%) of the coupling product, 2-benzyl-2-[(2,4-dioxopent-3-ylidene)aminooxy]malononitrile, has been achieved with the use of Cu(ClO4)2 · 6 H2O as oxidant. It is believed that the reaction involves intermediate formation of oxygen-centered aminoxyl radical.