Reaction of antiaromatic porphyrinoid with active methylene compounds

Abstract

Active methylene compounds which have two electron-withdrawing groups, such as ethyl 2-cyanoacetate, 3-oxobutanenitrile, cyclohexane-1,3-dione, malononitrile, pentane-2,4-dione, and ethyl acetoacetate, react regioselectively with antiaromatic norcorrolatonickel(II) in THF at room temperature in the presence of Cs₂CO₃ yielding new types of norcorrole derivatives retaining the spectral, magnetic, and redox properties of the starting macrocycle.