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

Abstract

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.

Afferent connections of the parvocellular subparafascicular thalamic nucleus in the rat: Evidence for functional subdivisions

“…An X‐ray crystallographic study showed that 1,2,3‐trithian‐5‐yl N ‐methylcarbamate ( 8 ) exists in the chair conformation with the substituent in the equatorial position 26. The hydrogen oxalate salt of 5‐( N , N ‐dimethylamino)‐1,2,3‐trithiane ( 9 ) is widely used as an insecticide 2, 27.…”

Heteroatom chemistry of cyclic benzopolychalcogenides: Synthesis and characterization

“…We also established a synthetic methodology for obtaining benzopenthiepins [13][14][15][16] and benzotrithioles [17,18] by the sulfurization-cyclization of the corresponding 1,2-benzenedithiols or their synthetic equivalents. substituents on the benzene ring were synthesized in good yields by the treatment of 1,2-benzenedithiol or 1,3-benzenedithiol-1,2-thione with elemental sulfur in liquid ammonia [13][14][15][16] (Scheme 1). These reactions were explained in the light of sulfurization by a new species generated from elemental sulfur in liquid ammonia.…”