Abstract
Publisher Summary This chapter explores the chemistry of both organic sulfur compounds and azaaromatic compounds, and discusses the chemical behaviors of organosulfur compounds of azaheteroaromatics, particularly pyridine and its related six-membered derivatives. The contents are divided into the following items: (1) a new concept of ligand-coupling reactions and ligand exchange within σ-sulfuranes formed in the reactions of the sulfoxides, bearing azaheteroaromatics, with grignard and organolithium reagents; (2) ipso substitution and desulfurization reactions of the sulfoxides and sulfones in which both the sulfinyl and the sulfonyl groups become good leaving groups; (3) thione-thiol tautomerism and its applications to the organic synthesis; and (4) miscellaneous reactions on the organosulfur compounds bearing azaheterocycles. Physicochemical behavior of these heteroaromatic systems is also compared to the corresponding aromatic systems. One remarkable feature is that the heteroaromatics bearing a sulfur atom are more reactive than the corresponding aromatic derivatives mainly because of the strong electron-releasing or withdrawing property of the heteroaromatics.
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