Reactions of 1-aryl-2,2,2-trifluoroethanone oximes with tetrasulfur tetranitride: Novel synthesis of 5-Aryl-5-trifluoromethyl-4H-1,3,2,4,6-dithiatriazines and 1-Aryl-2,2,2-trifluoroethanonylidenaminosulfenamides

Article abstract of DOI:10.1002/jhet.5570330214

The reactions of 1-aryl-2,2,2-trifluoroethanone oximes with tetrasulfur tetranitride (S₄N₄) in toluene at reflux gave 5-aryl-5-trifluoromethyl-4H-1,3,2,4,6-dithiatriazines 2, 1-aryl-2,2,2-trifluoroethanonylidenaminosulfenamides 3 and sulfur in 0-37%, 7-53%, and 2-41% yields, respectively. Treatment of 2 with tributyltin hydride in the presence of azobisisobutyronitrile in benzene at 80° afforded 3 in excellent yields.