R. A. Olofson, J. Landesberg, R. Berry
1966
Citations
0
Influential Citations
37
Citations
Journal
Tetrahedron
Abstract
Abstract 4-Phenyl-1,2-dithiolium perchlorate reacts with ammonia in ethanol to yield 4-phenyl-isothiazole. The reaction is general for dithiolium salts. When unsymmetrical dithiolium salts are treated with ammonia, the major product and, under many conditions, the only product is the 5-substituted isothiazole. Of the four possible mechanisms for these reactions, an addition-elimination mechanism has been shown to be correct. Treatment of dithiolium salts with hydroxylamine gives a mixture of isoxazoles and isothiazoles.