title: Dithiin
text: # Dithiin
  
  Dithiin /daɪ.ˈθaɪ.ɪn/ is a class of heterocyclic compounds, with the parent members having the formula $(C_2H_2)_2S_2.$ Two isomers of this parent are recognized, 1,2- and 1,4-dithiins. Planar dithiins are 8π $e^−$ systems, which would lead to antiaromaticity if the structure was planar. Akin to the behavior of cyclooctatetraene, they instead adopt nonplanar structures. Vinyldithiin, a common component of garlic, is a misnomer for 3-vinyl-4H-1,2-dithiin. 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 $HSCH_2CH(OEt)_2$ converts upon heating to the parent 1,4-dithiin. They are nonplanar and can be oxidized to their radical cations. Photolysis leads to dimerization via a [2+2] cycloaddition. Thianthrene is dibenzo-1,4-dithiin.
  
  ## 1,2-Dithiins
  
  1,2-Dithiins are isomers of but-2-ene-dithials. They tend to be unstable with respect to loss of sulfur and formation of the thiophene derivative:
  
      $C_4R_4S_2$ → $C_4R_4S$ + "S"
  
  They are often claret-colored. Some occur as flower pigments in plants of the family Asteraceae.
  
  