98203-30-6Relevant academic research and scientific papers
An unorthodox pathway to the 1,2-dithiin system
Huisgen, Rolf,Kalwinsh, Ivars,Moran, Joaquin R.,Noeth, Heinrich,Rapp, Jochen
, p. 1677 - 1684 (1997)
Tetracyanoethylene combines with two molecules of thiobenzophenone in refluxing benzene to give the tetrasubstituted 1,2-dithiin 8 (21-29%) besides the corresponding thiophene derivative 9 (40-52%). The X-ray analysis of the ruby-red 8 reveals a half-chair conformation with a torsion angle of 58.9° at the disulfide bond. The thermal desulfurization 8 → 9 (benzonitrile, 100°C) proceeds with t1/2 = 26.7 h, whereas the sulfur loss induced by triethyl phosphite is a billion times faster. The mechanisms of the formation of 8 and its sulfur extrusion are discussed in the light of recent literature. VCH Verlagsgesellschaft mbH, 1997.
