title: Synthesis, Characterization and Reactions of (Azidoethynyl)trimethylsilane.
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.
authors.affiliation: Organic Chemistry, Chemnitz University of Technology, Strasse der Nationen 62, Chemnitz 09111, Germany. klaus.banert@chemie.tu-chemnitz.de.
authors.forename: Klaus
authors.initials: K
authors.lastname: Banert
authors.affiliation: Organic Chemistry, Chemnitz University of Technology, Strasse der Nationen 62, Chemnitz 09111, Germany. manfred.hagedorn@chemie.tu-chemnitz.de.
authors.forename: Manfred
authors.initials: M
authors.lastname: Hagedorn
authors.affiliation: College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou Industrial Park, Suzhou 215123, China. 20144209141@stu.suda.edu.cn.
authors.forename: Zhuang
authors.initials: Z
authors.lastname: Wu
authors.affiliation: College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou Industrial Park, Suzhou 215123, China. xqzeng@suda.edu.cn.
authors.forename: Xiaoqing
authors.initials: X
authors.lastname: Zeng
mesh_terms: D000114:Acetylene / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: C000610807:(azidoethynyl)trimethylsilane; D000480:Alkynes; D001386:Azides; D014297:Trimethylsilyl Compounds; D000114:Acetylene
keywords: carbenes; ethynyl azides; gas phase IR data; photolysis; reactive intermediates