Potassium fluoride catalyzed reactions between malononitrile and α, β-unsaturated ketones

Abstract

The preparation and structure elucidation of the condensation products between malononitrile and a variety of α,β-unsaturated ketones using potassium fluoride as catalyst is described. If the carbonyl group of the α,β-unsaturated ketone is hindered, then Michael addition occurs. If, however, the carbonyl group is unencumbered, a Knoevenagel reaction appears to occur first which, in many cases, is then followed by conjugate addition and intramolecular condensation to yield compounds of unusual structure.