Reactions od Arylazosulfones with the Conjugate Bases of Active-Methylene Compounds

Article abstract of DOI:10.1016/0040-4020(95)00113-M

The reaction between arylazo p-tolyl sulfones 1a-f (Ar-N=N-SO2-p-Tol) and the potassium salts of some active-methylene compounds (CH2XY: X, Y = CN, COOEt) represents an example of unprecedented behaviour of azosulfones and effectively leads, depending on the nucleophile, to either unsymmetrical (6-8) or symmetrical (9) tetrasubstituted ethylenes.Of particular interest is the possibility to synthesize, in high yields and mild conditions, polarysed ethylenes some of which are otherwise not easily accessible.A mechanism involving successive condensation processes is supported by experimental evidence.