Mechanical Force for the Transformation of Aziridine into Imine

Sangmin Jung, Hyo Jae Yoon

    Research output: Contribution to journalArticlepeer-review

    16 Citations (Scopus)

    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 languageEnglish
    Pages (from-to)23564-23568
    Number of pages5
    JournalAngewandte Chemie - International Edition
    Volume60
    Issue number44
    DOIs
    Publication statusPublished - 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

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