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Chemical Consequences of the Mechanical Bond: A Tandem Active Template‐Rearrangement Reaction
Author(s) -
Modicom Florian,
Jamieson Ellen M. G.,
Rochette Elise,
Goldup Stephen M.
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201813950
Subject(s) - tandem , chemistry , rearrangement reaction , combinatorial chemistry , stereochemistry , catalysis , organic chemistry , materials science , composite material
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.