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  • The mechanism of the first step of the Mitsunobu reaction

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    Accepted Manuscript (AM)
    Author(s)
    Camp, David
    von Itzstein, Mark
    Jenkins, Ian D
    Griffith University Author(s)
    Jenkins, Ian D.
    von Itzstein, Mark
    Camp, David B.
    Year published
    2015
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    Abstract
    Previous DFT calculations employing phosphine (PH3) and dimethyl azodicarboxylate showed that a cyclic O,N-phosphorane was energetically favored relative to betaine formation. In this study strong experimental support for the formation of the phosphorane is described. The question of whether betaine formation occurs via nucleophilic attack of the phosphine on the azodicarboxylate as has been previously assumed, or via a [4 cycloaddition (cheletropic) reaction to give the O,N-phosphorane, followed by ring-opening to give the betaine has not been resolved. An answer to this intriguing question is provided.Previous DFT calculations employing phosphine (PH3) and dimethyl azodicarboxylate showed that a cyclic O,N-phosphorane was energetically favored relative to betaine formation. In this study strong experimental support for the formation of the phosphorane is described. The question of whether betaine formation occurs via nucleophilic attack of the phosphine on the azodicarboxylate as has been previously assumed, or via a [4 cycloaddition (cheletropic) reaction to give the O,N-phosphorane, followed by ring-opening to give the betaine has not been resolved. An answer to this intriguing question is provided.
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    Journal Title
    Tetrahedron
    Volume
    71
    DOI
    https://doi.org/10.1016/j.tet.2015.05.099
    Copyright Statement
    © 2015 Elsevier. Licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (http://creativecommons.org/licenses/by-nc-nd/4.0/) which permits unrestricted, non-commercial use, distribution and reproduction in any medium, providing that the work is properly cited.
    Subject
    Medicinal and biomolecular chemistry
    Organic chemistry
    Physical organic chemistry
    Publication URI
    http://hdl.handle.net/10072/69227
    Collection
    • Journal articles

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