Abstract
The application of aziridines as nonvulnerable mechanophores is reported. Upon exposure to a mechanical force, stereochemically pure nonactivated aziridines incorporated into the backbone of a macromolecule do not undergo cis–trans isomerization, thus suggesting retention of the ring structure under force. Nonetheless, aziridines react with a dipolarophile and seem not to obey conventional reaction pathways that involve C−C or C−N bond cleavage prior to the cycloaddition. Our work demonstrates that a nonvulnerable chemical structure can be a mechanophore.
Original language | English |
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Pages (from-to) | 4883-4887 |
Number of pages | 5 |
Journal | Angewandte Chemie - International Edition |
Volume | 59 |
Issue number | 12 |
DOIs | |
Publication status | Published - 2020 Mar 16 |
Keywords
- aziridines
- cycloaddition
- mechanochemistry
- mechanophores
- stereoselectivity
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)