Our group is interested in the chemistry of N-heterocycle-stabilized iodonium salts (NHIs), in which regard we systematically investigated pseudocyclic hydroxy(aryl)-NHIs as potent oxidizing reagents. Based on these initial findings, we were intended to systematically describe the chemistry of these potentially useful reagents and herein present a variety of novel (pseudo)cyclic ethynyl N-heterocycle-substituted- 3 -iodanes (ENHIs) and demonstrate their application in inter-and intramolecular group transfer reactions and in the synthesis of novel heteroaromatic compounds.