Thermal Stability of N-Heterocycle-Stabilized Iodanes – A Systematic Investigation

The thermal stability of pseudocyclic and cyclic N-heterocycle-stabilized (hydroxy)aryl- and mesityl(aryl)-l3-iodanes (NHIs) through thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) is investigated. NHIs bearing N-heterocycles with a high N/C-ratio such as triazoles show among the lowest descomposition temperatures and the highest decomposition energies. A comparison of NHIs with known (pseudo)cyclic benziodoxolones is made and we further correlated their thermal stability with reactivity in a model oxygenation.