The reactivity and the role of β-aryl-α-oxoglutaric acids in the oxidation of leucodrin and its derivatives by periodate

Abstract

The oxidation of ring-opened forms of leucodrin compounds by periodate is shown to proceed rapidly to yield the expected β-aryl-α-oxoglutaric acids, which are then more slowly cleaved to the corresponding β-arylsuccinic acids and carbon dioxide. The strong electrophilicity of the α-keto-carbon atoms of the former acids is demonstrated for the β-(p-hydroxyphenyl) analogue by its ready reaction with diazomethane to yield the corresponding oxiran derivatives.