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Updated: Mar 29, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Synthesis, Characterization and Reactions of (Azidoethynyl)trimethylsilane
Klaus Banert1, Manfred Hagedorn2, Zhuang Wu3
1Organic Chemistry, Chemnitz University of Technology, Strasse der Nationen 62, Chemnitz 09111, Germany. klaus.banert@chemie.tu-chemnitz.de.
Abstract:
Synthesis of azido(trimethylsilyl)acetylene (6) was performed by treating the iodonium salt 5 with highly soluble hexadecyltributylphosphonium azide (QN₃) at -40 °C. Although this product is very unstable, it can nevertheless be trapped by the click reaction with cyclooctyne to give the corresponding 1,2,3-triazole, and also directly characterized by ¹H- and (13)C-NMR data as well as IR-spectra, which were measured in solution at low temperature and in the gas phase. The thermal or photochemical decay of azide 6 leads to cyano(trimethylsilyl)carbene. This is demonstrated not only by quantum chemical calculations, but also by the trapping reactions with the help of isobutene.
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