The Chemistry of 1, 4-Dithiins

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Abstract
The advances of the chemistry of 1, 4-dithiins after the 1960's are reviewed. The preferred structure of 1, 4-dithiin has attracted considerable attention from both theoretical and experimental chemists. Although 1, 4-dithiin is comprised of a cyclic 8π-electron system, it is neither antiaromatic in character, nor aromatic as suggested earlier on the basis of possible d-orbital participation. The ring favors a boat structure and the chemical properties are predominantly olefinic. The olefinic carbon atoms as well as the sulfur atoms can enter into the reactions. Thus 1, 4-dithiin ring compounds provide versatile reactions not only with electrophiles but also with nucleophiles. In some thermal and photochemical reactions valence isomerizations, as encountered in the isoelectronic cyclooctatetraene, are involved as transient species. The synthetic routes to 1, 4-dithiin compounds are also covered.