Communication

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

  1. Prof. Dr. Klaus Banert1,*,
  2. René Arnold1,
  3. Dr. Manfred Hagedorn1,
  4. Philipp Thoss1,
  5. Prof. Dr. Alexander A. Auer2,3,*

Article first published online: 6 JUL 2012

DOI: 10.1002/anie.201203626

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 51, Issue 30, pages 7515–7518, July 23, 2012

Additional Information

How to Cite

Banert, K., Arnold, R., Hagedorn, M., Thoss, P. and Auer, A. A. (2012), 1-Azido-1-Alkynes: Synthesis and Spectroscopic Characterization of Azidoacetylene . Angew. Chem. Int. Ed., 51: 7515–7518. doi: 10.1002/anie.201203626

Author Information

  1. 1

    Technische Universität Chemnitz, Organische Chemie, Strasse der Nationen 62, 09111 Chemnitz (Germany) http://www.tu-chemnitz.de/chemie/org/index.html.en

  2. 2

    Max-Planck-Institut für Eisenforschung GmbH, Max-Planck-Strasse 1, 40237 Düsseldorf (Germany)

  3. 3

    New address: Max-Planck-Institut für Chemische Energiekonversion, Stiftstrasse 34–36, 45470 Mülheim an der Ruhr (Germany)

*Technische Universität Chemnitz, Organische Chemie, Strasse der Nationen 62, 09111 Chemnitz (Germany) http://www.tu-chemnitz.de/chemie/org/index.html.en

  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.

Publication History

  1. Issue published online: 18 JUL 2012
  2. Article first published online: 6 JUL 2012
  3. Manuscript Received: 10 MAY 2012

Funded by

  • Deutsche Forschungsgemeinschaft. Grant Number: BA 903/12-1

SEARCH

SEARCH BY CITATION

ARTICLE TOOLS

View Full Article with Supporting Information (HTML) Get PDF (345K)

Keywords:

  • carbenes;
  • ethynyl azides;
  • NMR spectroscopy;
  • quantum chemistry;
  • reaction mechanisms
Thumbnail image of graphical abstract

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.

View Full Article with Supporting Information (HTML) Get PDF (345K)