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Regioisomerism in Symmetric Dimethyl Dialdehydes Dictates their Photochemical Reactivity

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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Org. Chem. 2022, 87, 14, 9296-9300
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    Regioisomerism in Symmetric Dimethyl Dialdehydes Dictates their Photochemical Reactivity
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    • Florian Feist*
      Florian Feist
      Institute of Nanotechnology (INT), Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany
      *Email: [email protected]
      More by Florian Feist
      Orcidhttps://orcid.org/0000-0002-2051-5488
    • Leona L. Rodrigues
      Leona L. Rodrigues
      Centre for Materials Science, Queensland University of Technology, 2 George Street, Brisbane, Queensland 4000, Australia
      School of Chemistry and Physics, Queensland University of Technology, 2 George Street, Brisbane, Queensland 4000, Australia
      More by Leona L. Rodrigues
    • Sarah L. Walden
      Sarah L. Walden
      Centre for Materials Science, Queensland University of Technology, 2 George Street, Brisbane, Queensland 4000, Australia
      School of Chemistry and Physics, Queensland University of Technology, 2 George Street, Brisbane, Queensland 4000, Australia
      More by Sarah L. Walden
      Orcidhttps://orcid.org/0000-0002-7625-4010
    • Christopher Barner-Kowollik*
      Christopher Barner-Kowollik
      Institute of Nanotechnology (INT), Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany
      Centre for Materials Science, Queensland University of Technology, 2 George Street, Brisbane, Queensland 4000, Australia
      School of Chemistry and Physics, Queensland University of Technology, 2 George Street, Brisbane, Queensland 4000, Australia
      *Email: [email protected], [email protected]
      More by Christopher Barner-Kowollik
      Orcidhttps://orcid.org/0000-0002-6745-0570
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2022, 87, 14, 9296–9300
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    https://doi.org/10.1021/acs.joc.2c01020
    Published June 24, 2022
    Copyright © 2022 American Chemical Society
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    Abstract

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    We herein report the first light-driven selective monoderivatization (desymmetrization) of two chemically equivalent carbonyl groups in a single chromophore. By comparing of four symmetric regioisomers, featuring two equivalent ortho-methylbenzaldehyde units, we identify dimethyltherephtalaldehydes (DMTAs) which can be activated in a dual wavelength-selective fashion. Under visible light and UV-light irradiation, DMTAs undergo two consecutive Diels–Alder reactions exhibiting near-quantitative endo-selectivity (>99%) and provide excellent yields (96–98%). The influence of the regioisomerism of the dialdehydes on their photochemical behavior is profound, evidenced by an in-depth investigation of their photochemical performance. We exemplify the capability of the photosystems via the synthesis of complex Diels–Alder adducts with various dienophiles, including alkynes.

    Copyright © 2022 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.joc.2c01020.

    • Materials, instrumentation, synthetic procedures, photoreactions, copies of UV–vis, fluorescence and NMR specta, and LCMS results (PDF)

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    • FAIR data, including the primary NMR FID files, for compounds 3a–d (ZIP)

    • FAIR data, including the primary NMR FID files, for compounds 4a–f (ZIP)

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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2022, 87, 14, 9296–9300
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.2c01020
    Published June 24, 2022
    Copyright © 2022 American Chemical Society
    Request reuse permissions

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