Oxidation of benzaldehyde semicarbazone by Tl(III) acetate—a structure reactivity correlation

Abstract

The kinetics of Tl(III) acetate oxidation of semicarbazones of benzaldehyde and substituted benzaldehydes have been investigated in aqueous (90%) acetic acid. Electron-releasing substituents in the phenyl ring enhance the rate of the reaction, whereas electron-withdrawing substituents retard the rate. The rho value of −1 favours electron-deficient transition state. To account for the major product of the reaction,viz respective benzaldehyde, a suitable scheme involving N-thallated intermediate has been proposed