Chemical Consequences of the Mechanical Bond: A Tandem Active Template-Rearrangement Reaction.
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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.
SUBMITTER: Modicom F
PROVIDER: S-EPMC6589916 | biostudies-literature |
REPOSITORIES: biostudies-literature
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