A GENERAL, REGIOSELECTIVE SYNTHESIS OF 2-ALKENYLANILINES

Reduction of selected 2,1-benzothiazines with sodium amalgam leads to the formation of 2-alkenylanilines in high yield. The benzothiazines a re readily available from the reaction of N-phenyl-S-(p-tolyl)sulfonim idoyl chloride with alkynes in the presence of aluminum chloride. The sulfonimidoyl chloride is derived from aniline, and the process descri bed herein thus constitutes a high-yielding, regioselective functional ization of aniline.