Synthesis and structural characterization of cis- and trans-fused 4a,5,6,7,8,8a-hexahydro-2H,4H-1,3-benzodithiines and their 2-methyl and 2,2-dimethyl derivatives.

Both cis- and trans-fused 4a,5,6,7,8,8a-hexahydro-2H,4H-1,3-benzodithiine together with their 2-methyl and 2,2-dimethyl derivatives were prepared as racemates from the appropriate dithiols obtained via multistep syntheses. The products were characterized by 1 H and 13 C NMR, mass spectrometry, and for two of the cis-fused compounds by X-ray diffraction. 1 H, 1 H vicinal coupling constants indicated that all compounds attain chair-chair conformations as their predominant conformations. All three trans-fused isomers exist in totally biased chair-chair conformations and are essentially conformationally locked, whereas the cis-fused compounds are conformationally mobile and can potentially atta…