Abstract
Vinylogy, is a well-known concept of the retention of the chemical properties, such as reactivity, through the double bond. The vinylogous amide has been studied for a long time, however, the compounds with the amide bond intervented by the aromatic group has been rarely studied. In this presentation, we will report the synthesis and chemical properties of "aromatic vinylogous" amide compounds.
First, we synthesized the aromatic amide compounds by the Buchwald-Hartwig cross coupling. The structures of these compounds were studied by the X-ray crystallography to compare the bond length to estimate the effect of the resonance. The ortho and para substituted compounds showed the effect of resonance compared to the meta substituted analogue. In addition, carbonyl group of ortho and meta substituted compounds was less reactive toward the reduction by sodium borohydride compared to the meta substituted compound.
