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    The role of substituents in retro Diels-Alder extrusion of CO2 from 2(H)-pyrone cycloadducts

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    Abdullahi_et_al_tetrahedron.pdf (662.7Kb)
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    Publication date
    2016-10-06
    Author
    Abdullahi, Mohamed H.
    Thompson, L.M.
    Bearpark, M.J.
    Vinader, Victoria
    Afarinkia, Kamyar
    Keyword
    Extrusion of CO2; Diels-Alder cycloaddition; 2(H)-pyrone; DFT; Synthesis; Role of substituents
    Peer-Reviewed
    Yes
    
    Metadata
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    Abstract
    An experimental and computational investigation is conducted into the role of substituents in retro Diels-Alder extrusion of CO2 from 2-oxa-bicyclo[2.2.2]oct-5-en-3-ones. We provide the first experimental evidence that loss of CO2 from the cycloadducts significantly depends on the nature and position of the substituents. For example, we show that whilst 5-carboethoxy-2-pyrone undergoes a more facile cycloaddition that 3-carboethoxy-2-pyrone, the cycloadduct from the latter pyrone undergoes a more facile loss of CO2 than the cycloadduct from the former pyrone.
    URI
    http://hdl.handle.net/10454/9888
    Version
    Accepted manuscript
    Citation
    Abdullahi MH, Thompson LM, Bearpark MJ et al (2016) The role of substituents in retro Diels–Alder extrusion of CO2 from 2(H)-pyrone cycloadducts. Tetrahedron. 72(40): 6021-6024.
    Link to publisher’s version
    http://dx.doi.org/10.1016/j.tet.2016.07.066
    Type
    Article
    Collections
    Life Sciences Publications

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