Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 12, Pages 4883-4887Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201915438
Keywords
aziridines; cycloaddition; mechanochemistry; mechanophores; stereoselectivity
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Funding
- NRF of Korea [NRF-2016R1D1A1A02937504, NRF-2019R1A6A1A11044070, NRF-2019R1A2C2011003]
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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.
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