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 1H 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.
| Original language | English |
|---|---|
| Pages (from-to) | 23564-23568 |
| Number of pages | 5 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 60 |
| Issue number | 44 |
| DOIs | |
| Publication status | Published - 2021 Oct 25 |
Bibliographical note
Funding Information:This research was supported by NRF Korea (NRF-2016R1D1A1A02937504; NRF-2019R1A2C2011003 and NRF-2019R1A6A1A11044070) and the Industrial Strategic Technology Development Program-Alchemist Project (20012390, 4D MONALISA) funded By the Ministry of Trade, Industry & Energy (MOTIE, Korea). The authors are grateful for the NMR facility in the Institute for Basic Science (IBS) Center for Molecular Spectroscopy and Dynamics.
Funding Information:
This research was supported by NRF Korea (NRF‐2016R1D1A1A02937504; NRF‐2019R1A2C2011003 and NRF‐2019R1A6A1A11044070) and the Industrial Strategic Technology Development Program‐Alchemist Project (20012390, 4D MONALISA) funded By the Ministry of Trade, Industry & Energy (MOTIE, Korea). The authors are grateful for the NMR facility in the Institute for Basic Science (IBS) Center for Molecular Spectroscopy and Dynamics.
Publisher Copyright:
© 2021 Wiley-VCH GmbH
Keywords
- aziridines
- mechanochemistry
- polymers
- reaction mechanisms
- structure elucidation
ASJC Scopus subject areas
- Catalysis
- General Chemistry