Polarographic Studies in Acetonitrile and Dimethylformamide: IX . Behavior of α,β‐Unsaturated Carbonyl Compounds

Abstract

Benzalacetophenone, benzalacetone, cinnamaldehyde, and crotonaldehyde were reduced stepwise at the dropping mercury electrode in anhydrous dimethylformamide. Large‐scale electrolytic reductions were performed on the compounds in the presence and absence of carbon dioxide. Carbonation of the dianions of benzalacetophenone and benzalacetone gave α‐phenyl‐β‐benzoyl propionic acid and α‐phenyllevulinic acid, respectively. In the absence of carbon dioxide, the dianion of benzalacetophenone gave a polymer. The anion‐free radical of benzalacetophenone in the presence of carbon dioxide gave a monomeric dicarboxylic acid and a dimeric monocarboxylic acid. In the absence of carbon dioxide a trimer was obtained. The reduction of cinnamaldehyde and crotonaldehyde gave tars.