We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Chemical Consequences of the Mechanical Bond: A Tandem Active Template‐Rearrangement Reaction.
- Authors
Modicom, Florian; Jamieson, Ellen M. G.; Rochette, Elise; Goldup, Stephen M.
- Abstract
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.
- Subjects
REARRANGEMENTS (Chemistry); CHEMICAL bonds; CHEMICAL templates; ACRYLAMIDE; TRIAZOLES
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 12, p3915
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201813950