Impacts of Chalcogen Bonding on the Stability and Reactivity of 5-Iminothianthrene Platform: Toward Electrophilic Nitrogen Sources.

The thianthrene scaffold has recently attracted significant attention in various coupling reactions. Although 5-iminothianthrene and its derivatives are expected to function as electrophilic aminating reagents, their properties and reactivity have not been fully investigated. In this work, it was found that 5-iminothianthrene reacted with various electrophiles, such as acid chlorides, protons, and isothiocyanates to give the corresponding adducts. In addition, intramolecular chalcogen bonding (ChB) was identified in those adducts, and this interaction was found to contribute to their stability and reactivity. Finally, the potential of N-acyliminothianthrenes as N-acylnitrene equivalents was demonstrated.