Elimination–addition. Part IX. Reactions of p-toluoylacetylene and p-toluoylacetaldehyde with α-phenylethylamine

Abstract

α-Phenylethylamine reacts with p-toluoylacetylene and with p-toluoylacetaldehyde to give the same product which is shown, by proton magnetic resonance spectroscopy, to be a mixture of cis- and trans-β-[1-phenylethylaminovinyl]p-tolyl ketones. These isomers have been separated and their interconversion has been examined by polarimetric and ultraviolet spectrophotometric methods.

Our observations are in accord with our earlier work but at variance with a recent Russian report in which one of the isomers is described as an enol-imine rather than a keto-enamine.