Recently we have observed that hydrazones react with sulfonium salts (i.e. “activated” DMSO) to give either alkyl chlorides or diazo compounds depending upon the reaction conditions. We have also discovered that N-monosubstituted hydrazones containing a pendant alkene (e.g. 1) reacted with dimethyl sulfide ditriflate to provide a diazenium salt (e.g. 2). Our preliminary results concerning the efficiency and scope of these transformations and mechanistic hypotheses for these transformations will be discussed.