Mechanical Force Induces Ylide-Free Cycloaddition of Nonscissible Aziridines
- Authors
- Jung, Sangmin; Yoon, Hyo Jae
- Issue Date
- 16-3월-2020
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- aziridines; cycloaddition; mechanochemistry; mechanophores; stereoselectivity
- Citation
- ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.59, no.12, pp.4883 - 4887
- Indexed
- SCIE
SCOPUS
- Journal Title
- ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Volume
- 59
- Number
- 12
- Start Page
- 4883
- End Page
- 4887
- URI
- https://scholar.korea.ac.kr/handle/2021.sw.korea/57262
- DOI
- 10.1002/anie.201915438
- ISSN
- 1433-7851
- 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.
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