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Open AccessCommunication

Synthesis, Characterization and Reactions of (Azidoethynyl)trimethylsilane

Organic Chemistry, Chemnitz University of Technology, Strasse der Nationen 62, Chemnitz 09111, Germany
College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou Industrial Park, Suzhou 215123, China
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Molecules 2015, 20(12), 21328-21335;
Received: 9 November 2015 / Revised: 20 November 2015 / Accepted: 23 November 2015 / Published: 1 December 2015
(This article belongs to the Special Issue Organic Azides)
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 13C-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. View Full-Text
Keywords: carbenes; ethynyl azides; gas phase IR data; photolysis; reactive intermediates carbenes; ethynyl azides; gas phase IR data; photolysis; reactive intermediates
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MDPI and ACS Style

Banert, K.; Hagedorn, M.; Wu, Z.; Zeng, X. Synthesis, Characterization and Reactions of (Azidoethynyl)trimethylsilane. Molecules 2015, 20, 21328-21335.

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