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1-Azido-1-Alkynes: Synthesis and Spectroscopic Characterization of Azidoacetylene

Banert, Klaus ; Arnold, René ; Hagedorn, Manfred ; Thoss, Philipp ; Auer, Alexander A.

Angewandte Chemie (International ed.), 2012-07, Vol.51 (30), p.7515-7518 [Periódico revisado por pares]

Weinheim: WILEY-VCH Verlag

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  • Título:
    1-Azido-1-Alkynes: Synthesis and Spectroscopic Characterization of Azidoacetylene
  • Autor: Banert, Klaus ; Arnold, René ; Hagedorn, Manfred ; Thoss, Philipp ; Auer, Alexander A.
  • Assuntos: carbenes ; Cleavage ; Cycloaddition ; ethynyl azides ; Explosions ; NMR spectroscopy ; quantum chemistry ; reaction mechanisms ; Spectroscopy ; Synthesis ; Triazoles
  • É parte de: Angewandte Chemie (International ed.), 2012-07, Vol.51 (30), p.7515-7518
  • Notas: ArticleID:ANIE201203626
    Deutsche Forschungsgemeinschaft - No. BA 903/12-1
    We gratefully acknowledge financial support from the Deutsche Forschungsgemeinschaft (BA 903/12-1). We thank Dr. O. Jaurich (Mettler Toledo) and Dr. S. Hemeltjen (TU Chemnitz) for their help in the measurement of low-temperature IR spectra, as well as A. Käßner and Dr. A. Ihle for the realization of some experiments and assistance with preparing the manuscript. Dedicated to Professor K. Barry Sharpless, who inspired us to bring alkynes and azides together. Reactions of Unsaturated Azides, Part 30; for Part 29, see: K. Banert, C. Berndt, M. Hagedorn, H. Liu. T. Anacker, J. Friedrich, G. Rauhut, Angew. Chem. 2012, 124, 4796-4800; Angew. Chem. Int. Ed. 2012, 51, 4718-4721.
    istex:FB32EC87CB1F3BF9DBC09BA1CD6ECFFA736BD243
    ark:/67375/WNG-TFWF73JQ-M
    Angew. Chem.
    124
    4796–4800
    Angew. Chem. Int. Ed.
    2012
    4718–4721.
    ,
    51
    We gratefully acknowledge financial support from the Deutsche Forschungsgemeinschaft (BA 903/12‐1). We thank Dr. O. Jaurich (Mettler Toledo) and Dr. S. Hemeltjen (TU Chemnitz) for their help in the measurement of low‐temperature IR spectra, as well as A. Käßner and Dr. A. Ihle for the realization of some experiments and assistance with preparing the manuscript. Dedicated to Professor K. Barry Sharpless, who inspired us to bring alkynes and azides together. Reactions of Unsaturated Azides, Part 30; for Part 29, see: K. Banert, C. Berndt, M. Hagedorn, H. Liu. T. Anacker, J. Friedrich, G. Rauhut
    ObjectType-Article-1
    SourceType-Scholarly Journals-1
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  • Descrição: Sleeping Beauty awakes: After 102 years of unsuccessful attempts to synthesize azidoacetylene, spectroscopic evidence for this compound has been shown. This highly explosive compound was synthesized by the treatment of ethynyliodonium salts with azide (QN3=n‐C16H33Bu3PN3). Azidoacetylene can be trapped by a cycloaddition reaction to yield a stable triazole, otherwise cleavage to generate cyanocarbene dominates.
  • Editor: Weinheim: WILEY-VCH Verlag
  • Idioma: Inglês

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