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)-λ 3 -iodanes (NHIs) through thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) is investigated. Peak decomposition temperatures ( T peak ) were observed within a wide...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2019-09, Vol.15 (1), p.2311-2318
Main Authors: Boelke, Andreas, Vlasenko, Yulia A, Yusubov, Mekhman S, Nachtsheim, Boris J, Postnikov, Pavel S
Format: Article
Language:English
Subjects:
Chemistry
Decomposition
Differential scanning calorimetry
Full Research Paper
hypervalent iodine
Investigations
Iodine
Ligands
n-heterocycle
Oxygenation
stability
Thermal stability
thermogravimetry
Triazoles
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Summary:The thermal stability of pseudocyclic and cyclic N -heterocycle-stabilized (hydroxy)aryl- and mesityl(aryl)-λ 3 -iodanes (NHIs) through thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) is investigated. Peak decomposition temperatures ( T peak ) were observed within a wide range between 120 and 270 °C. Decomposition enthalpies (Δ H dec ) varied from −29.81 to 141.13 kJ/mol. A direct comparison between pseudocyclic and cyclic NHIs revealed high T peak but also higher Δ H dec values for the latter ones. NHIs bearing N -heterocycles with a high N/C-ratio such as triazoles show among the lowest T peak and the highest Δ H dec values. A comparison of NHIs with known (pseudo)cyclic benziodoxolones is made and we further correlated their thermal stability with reactivity in a model oxygenation.
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.15.223