Abstract
The reaction between arylazo p-tolyl sulfones la-f (Ar-N=N-SO 2p-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 lArNHCX=CXY: X = Y = CN (6) or X = COOEt, Y = CN (7)] some of which are otherwise not easily accessible. A mechanism involving successive condensation processes is supported by experimental evidence.
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