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dithiin
Dithiin is a class of heterocyclic compounds, with the parent members having the formula (C2H2)2S2. Two isomers of this parent are recognized, 1,2- and 1,4-dithiins. These compounds are antiaromatic consisting of 8π e− systems, akin to cyclooctatetraene. Vinyldithiin, a common component of garlic, is a misnomer for 3-vinyl-4''H''-1,2-dithiin, since true 1,3-dithiins are unknown.
==1,4-Dithiins==
1,4-Dithiins have been more extensively studied. They are usually prepared by condensation of the equivalent of α-mercaptocarbonyls. For example, the acetal HSCH2CH(OEt)2 converts upon heating to the parent 1,4-dithiin. Being antiaromatic, they are nonplanar and can be oxidized to their radical cations. Photolysis leads to dimerization via a () cycloaddition.〔Keiji Kobayashia & Chhabi L. Gajurela "The Chemistry of 1, 4-Dithiins" Sulfur Reports, 1986, Volume 7, pp. 123-148. 〕 Thianthrene is dibenzo-1,4-dithiin.
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