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Click reactions with pseudo-geminal bis(azido-methylene)[2.2]paracyclophane

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Abstract

The regioselective copper-catalyzed cycloaddition reactions of pseudo-geminal bis(azido-methylene)[2.2]paracyclophane with terminal alkynes have provided the corresponding pseudo-geminal bis(1,2,3-triazoles). The precursor bis(azide) was synthesized from the corresponding pseudo-geminal bis(bromide) and sodium azide by a solvent-dependent reaction. X-ray structural analyses of the addition products demonstrate that the corresponding click reactions proceed regioselectively.

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Acknowledgements

L. M. B. is indebted to the Alexander von Humboldt Foundation for a stay in Braunschweig. This work was supported by a grant of the Romanian National Authority for Scientific Research, CNDI–UEFISCDI, project number 51/2012. Part of this work was supported by a grant of the Alexandru Ioan Cuza University of Iasi—Grants for Young Researchers of UAIC—project number 07/03.12.2015.

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Authors and Affiliations

  1. Department of Chemistry, “Al. I. Cuza” University of Iasi, 11 Carol I Bv., 700506, Iasi, Romania

    Sergiu Pavel, Iuliean V. Asaftei, Laura G. Sarbu & Lucian M. Birsa

  2. Institute of Organic Chemistry, Technical University of Braunschweig, Hagenring 30, 38106, Braunschweig, Germany

    Henning Hopf

  3. Institute of Inorganic and Analytical Chemistry, Technical University of Braunschweig, Hagenring 30, 38106, Braunschweig, Germany

    Peter G. Jones

Authors
  1. Sergiu Pavel
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  2. Henning Hopf
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  3. Peter G. Jones
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  4. Iuliean V. Asaftei
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  5. Laura G. Sarbu
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  6. Lucian M. Birsa
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Corresponding author

Correspondence to Lucian M. Birsa.

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Pavel, S., Hopf, H., Jones, P.G. et al. Click reactions with pseudo-geminal bis(azido-methylene)[2.2]paracyclophane. Monatsh Chem 147, 2179–2183 (2016). https://doi.org/10.1007/s00706-016-1842-3

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  • DOI: https://doi.org/10.1007/s00706-016-1842-3

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