Collect. Czech. Chem. Commun. 1985, 50, 2260-2264

Benzylidenemalonaldehydes: A redox reaction during the attempted cycloaddition on nitrosobenzene

Dalimil Dvořák, Miloš Buděšínský, David Šaman and Zdeněk Arnold

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Reaction of p-chlorobenzylidenemalonaldehyde with nitrosobenzene represents a reduction-oxidation process leading to 2-formyl-3-anilino-3-(4-chlorophenyl)acrylic acid (III). The structure of the product, including two intramolecular hydrogen bonds, has been proved by analysis of the 1H and 13C NMR spectra of the acid III, its deuterated form and the methyl ester obtained by reaction with diazomethane.