Mechanical Force for the Transformation of Aziridine into Imine
- Authors
- Jung, Sangmin; Yoon, Hyo Jae
- Issue Date
- 25-10월-2021
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- aziridines; mechanochemistry; polymers; reaction mechanisms; structure elucidation
- Citation
- ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.60, no.44, pp.23564 - 23568
- Indexed
- SCIE
SCOPUS
- Journal Title
- ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Volume
- 60
- Number
- 44
- Start Page
- 23564
- End Page
- 23568
- URI
- https://scholar.korea.ac.kr/handle/2021.sw.korea/136013
- DOI
- 10.1002/anie.202109358
- ISSN
- 1433-7851
- Abstract
- Force-selective mechanochemical reactions may be important for applications in polymer mechanochemistry, yet it is difficult to achieve such reactions. This paper reports that cis-N-phthalimidoaziridine incorporated into a macromolecular backbone undergoes migration of N-phthalimido group to afford imine under mechanochemical condition and not thermal one. The imine is further hydrolyzed by water bifurcating into amine and aldehyde. These structural transformations are confirmed by H-1 NMR and FT-IR spectroscopic analyses. Computational simulations are conducted for the aziridine mechanophore to propose the mechanism of reaction and define the substrate scope of reaction.
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