Abstract Prolonged heating of a series of α-hydroxy-α-aryl-o-toluidines in the presence of base and carbon disulfide afforded the corresponding 4H-3,]-benzothiazine-2-thiones. Treatment of the thiolalkyl ethers of these compounds with strong bases led to ring contraction to the corresponding 2-thioalkyl indole with concommitant extrusion of sulfur. The scope of the reaction was examined.