Synthesis, Characterization and Reactions of AzidoethynyltrimethylsilaneReport as inadecuate




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1

Organic Chemistry, Chemnitz University of Technology, Strasse der Nationen 62, Chemnitz 09111, Germany

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College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou Industrial Park, Suzhou 215123, China





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Academic Editor: Derek J. McPhee

Abstract Synthesis of azidotrimethylsilylacetylene 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 cyanotrimethylsilylcarbene. 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





Author: Klaus Banert 1,* , Manfred Hagedorn 1, Zhuang Wu 2 and Xiaoqing Zeng 2,*

Source: http://mdpi.com/



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