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

Florian ModicomEllen M G JamiesonElise RochetteStephen Michael Goldup
Published in: Angewandte Chemie (International ed. in English) (2019)
We report the unexpected discovery of a tandem active template CuAAC-rearrangement process, in which N2 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 CuI -triazolide intermediate of the CuAAC reaction and diverts it down the rearrangement pathway; when no mechanical bond is formed, the CuAAC product is isolated.
Keyphrases
  • electron transfer
  • molecularly imprinted
  • transition metal
  • high throughput
  • single cell