Unusual reaction of chloramine-T with araldoximes

J Org Chem. 2003 Feb 21;68(4):1567-70. doi: 10.1021/jo020473j.

Abstract

Reaction of araldoximes with 4 equiv of chloramine-T in refluxing methanol produces N-(p-tolyl)-N-(p-tosyl)benzamides via addition of 2 equiv of chloramine-T to the intermediate nitrile oxide followed by extrusion of sulfur dioxide.