Mercury(II) acetate-assisted oxidative hydrolysis of thiosemicarbazones of benzaldehyde, acetophenone and benzophenone by potassium bromate

Abstract

Thiosemicarbazones of benzaldehydes, acetophenones and benzophenones are oxidatively hydrolysed by potassium bromate, {Br^v}, in the presence of mercury(II) acetate, as Hg^II forms a complex with sulphur atoms, increasing the lability of the N–H bond. The rates of these reactions are less susceptible to the electronic influence of the substituents at the phenyl ring compared with other oxidants, showing that N-bromate ester formation is the rate-determining step of this reaction. Such N-bromate ester formation seems to occur more readily with Hg^II-sulphur complexes.