Thermal stability of N-heterocycle-stabilized iodanes-A systematic investigation

Andreas Boelke, Yulia A. Vlasenko, Mekhman S. Yusubov, Boris J. Nachtsheim, Pavel S. Postnikov

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The thermal stability of pseudocyclic and cyclic N-heterocycle-stabilized (hydroxy)aryl-and mesityl(aryl)-λ3-iodanes (NHIs) through thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) is investigated. Peak decomposition temperatures (Tpeak) were observed within a wide range between 120 and 270 °C. Decomposition enthalpies (ΔHdec) varied from-29.81 to 141.13 kJ/mol. A direct comparison between pseudocyclic and cyclic NHIs revealed high Tpeak but also higher ΔHdec values for the latter ones. NHIs bearing N-heterocycles with a high N/C-ratio such as triazoles show among the lowest Tpeak and the highest ΔHdec 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.

Original languageEnglish
Pages (from-to)2311-2318
Number of pages8
JournalBeilstein Journal of Organic Chemistry
Volume15
DOIs
Publication statusPublished - 27 Sep 2019

Keywords

  • Differential scanning calorimetry
  • Hypervalent iodine
  • N-heterocycle
  • Stability
  • Thermogravimetry

ASJC Scopus subject areas

  • Organic Chemistry

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