Chemical Consequences of the Mechanical Bond: A Tandem Active Template-Rearrangement Reaction

Florian Modicom, Ellen M.G. Jamieson, Elise Rochette, Stephen M. Goldup*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)


We report the unexpected discovery of a tandem active template CuAAC-rearrangement process, in which N 2 is extruded on the way to the 1,2,3-triazole product to give instead acrylamide rotaxanes. Mechanistic investigations suggest this process is dictated by the mechanical bond, which stabilizes the Cu I -triazolide intermediate of the CuAAC reaction and diverts it down the rearrangement pathway; when no mechanical bond is formed, the CuAAC product is isolated.

Original languageEnglish
Pages (from-to)3875-3879
Number of pages5
JournalAngewandte Chemie - International Edition
Issue number12
Publication statusPublished - 18 Mar 2019

Bibliographical note

Funding Information:
The authors acknowledge the use of the IRIDIS High Performance Computing Facility, and associated support services at the University of Southampton. The authors thank Fluorochem for the gift of reagents. S.M.G. acknowledges funding from the European Research Council (Con- solidator Grant Agreement no. 724987), and Leverhulme Trust (ORPG-2733). S.M.G. thanks the Royal Society for a Research Fellowship. E.M.G.J. and F.M. thank the University of Southampton and EPSRC for financial support (EP/ M508147/1).

Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim


  • mechanical bonds
  • rearrangement
  • rotaxanes
  • supramolecular chemistry
  • triazoles

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry


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