Optimization of the synthesis of symmetric aromatic tri- and tetrasulfides

The reaction of aromatic thiols with sulfur dichloride and sulfur monochloride to form the corresponding aromatic trisulfides, 2a-d, and tetrasulfides, 3a-d, has been optimized with respect to yield and purity. The use of pyridine as an amine base and the use of freshly distilled sulfur monochloride (S(2)Cl(2)) serve as important alterations to the synthetic method. Their physical properties have been characterized, revealing some discrepancies with the literature.