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 r...

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Detalles Bibliográficos
Autores principales: Boelke, Andreas, Vlasenko, Yulia A, Yusubov, Mekhman S, Nachtsheim, Boris J, Postnikov, Pavel S
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2019
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6774080/
https://www.ncbi.nlm.nih.gov/pubmed/31598183
http://dx.doi.org/10.3762/bjoc.15.223
Descripción
Sumario: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 (ΔH(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 ΔH(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 ΔH(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.

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