Synthesis of Cyclic Polysulfides. Reactions of Dithiols and Related Compounds with Elemental Sulfur in Liquid Ammonia

Article abstract of DOI:10.1246/bcsj.61.1647

Many cyclic polysulfides, i.e., benzopentathiepins (3a-d), 6H-1,2,3,4,5-benzopentathiocin, 5H-1,2,3,4-benzotetrathiepin, 3H-1,2-benzodithiole, 1,5-dihydro-2,3,4-benzotrithiepin, 1,4-dihydro-2,3-benzodithiin, naphtho<1,8-cd>-1,2-dithiole, 1,2,3-trithiane, 1,2-dithiane, 2,3,4,5-tetrathiabicyclo<4.4.0>decane, and 2,3,4,5,6-pentathiabicyclo<5.4.0>undecane, were synthesized in high yields by new reactions of their corresponding dithiols and related compounds, 1,3-benzodithiole-2-thiones (5) and 1,3-dithiolane-2-thione, with elemental sulfur in liquid ammonia at ambient temperature.In the synthesis of 3a-d from 1,2-benzenedithiol or 5, considerable increase in the product yield was observed upon adding 1,3-dinitrobenzene to the solvent used in work-up.