Chemical Consequences of the Mechanical Bond: A Tandem Active Template‐Rearrangement Reaction
| Autor: | Florian Modicom, Ellen M. G. Jamieson, Elise M. Rochette, Stephen M. Goldup |
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| Jazyk: | angličtina |
| Předmět: |
Rotaxane
Mechanical bond Tandem 010405 organic chemistry Communication rearrangement Triazole Supramolecular chemistry General Chemistry General Medicine 010402 general chemistry Combinatorial chemistry 01 natural sciences Catalysis Communications Supramolecular Chemistry 0104 chemical sciences chemistry.chemical_compound rotaxanes chemistry Product (mathematics) Acrylamide Rearrangement reaction mechanical bonds triazoles |
| Zdroj: | Angewandte Chemie International Edition Angewandte Chemie (International Ed. in English) |
| ISSN: | 1521-3773 1433-7851 |
| DOI: | 10.1002/anie.201813950 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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