Abstract
Publisher Summary The chemistry of heteroaromatic iminium compounds is very complex due to the large variability of N-heteroaromatic rings and N-substituents. This chapter describes the principles of oxidative transformation of pyridinium salts based on publications of the last 20 years and the oxidation of several other heteroaromatic iminium compounds. The chapter discusses the pyridinium salts. In a study concerning the kinetics and mechanism of osmium tetroxide-catalyzed ferricyanide oxidation of pyridinium and quinolinium salts it was found that the rates of reaction are first order with respect to substrate, alkali, and catalyst, and zero order with respect to ferricyanide concentration. From this result a suitable mechanism has been proposed, which involves the rate-determining formation of a certain complex, which rapidly decomposes to give pyridone and osmium. As the reaction is influenced by the dielectric constant of the solvent and shows a positive salt effect, the existence of radical intermediates is ruled out and an ionic mechanism is favored.
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