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Molecules 2015, 20(12), 21328-21335; doi:10.3390/molecules201219770

Synthesis, Characterization and Reactions of (Azidoethynyl)trimethylsilane

1
Organic Chemistry, Chemnitz University of Technology, Strasse der Nationen 62, Chemnitz 09111, Germany
2
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
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)
View Full-Text   |   Download PDF [1240 KB, uploaded 1 December 2015]   |  

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 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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