S-tosylsulfenamides, new electrophilic sulfosulfenylating agents
摘要:
A method has been developed for the synthesis of thiosulfonates by the electrophilic addition of S-tosylsulfenamides to ole-fins or their electrophilic substitution in aromatic systems. SO3, Py.SO3, and BF3.Et2O were used as activators. The addition of S-tosylsulfenamides to olefins proceeds through electrophilic trans addition.
A trifluoroacetic-acid-mediated desulfurilative sulfonylthiolation of arenes using SS-morpholino dithiosulfonate is described. This system is based on selective activation of the morpholino group over the tosyl group of the doubly transformable sulfur surrogate. Mechanistic studies suggested that the reaction proceeds through electrophilic aromatic substitution followed by sulfur extrusion. The wide
The reactions of diamino disulfides (2) and diamino sulfides (3) with p-toluenesulfinic acid (1) were found to give new types of compounds, amino p-toluenesulfonyl disulfides (5) and amino p-toluenesulfonyl sulfides (10), respectively. On the other hand, the reaction between dimorpholino sulfoxide (4) and 1 gave p-toluenesulfinylmorpholide (13).