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    A Computational and Experimental Investigation of the Diels-Alder Cycloadditions of Halogen Substituted 2(H)-pyran-2-one

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    Publication date
    2003
    Author
    Afarinkia, Kamyar
    Bearpark, M.J.
    Ndibwami, A.
    Keyword
    Computational
    Diels-Alder Cycloadditions
    4-Chloro-2(H)-pyran-2-one
    Electron-deficient dienophiles
    Stereoselectivity
    Density functional theory
    Peer-Reviewed
    Yes
    
    Metadata
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    Abstract
    4-Chloro-2(H)-pyran-2-one undergoes thermal Diels−Alder cycloaddition with electron-deficient dienophiles to afford, without any significant selectivity, 6-endo- and 5-endo-substituted bicyclic lactone cycloadducts. In contrast to 3- and 5-bromo-2(H)-pyran-2-one, 4-chloro-2(H)-pyran-2-one does not undergo thermal cycloadditions with electron-rich dienophiles. The regio- and stereochemical preferences of the cycloadditions of 4-chloro-2(H)-pyran-2-one and other related 2(H)-pyran-2-ones are investigated computationally. Calculations were carried out on the transition states leading to the four possible regio- and stereoisomeric cycloadducts using density functional theory (B3LYP/6-31G*). These studies allow prediction of the regio- and stereoselectivity in these reactions which are in line with experimental observations.
    URI
    http://hdl.handle.net/10454/2366
    Version
    No full-text in the repository
    Citation
    Afarinkia, K., Bearpark, M. J., Ndibwami, A. (2003) A Computational and Experimental Investigation of the Diels-Alder Cycloadditions of Halogen Substituted 2(H)-pyran-2-one. The Journal of Organic Chemistry. 68 (19): 7158-7166.
    Link to publisher’s version
    https://doi.org/10.1021/jo0348827
    Type
    Article
    Collections
    Life Sciences Publications

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