Applications of Di-π-Methane and Related Rearrangement Reactions in Chemical Synthesis

Martin G. Banwell*, David J.Y.D. Bon

*Corresponding author for this work

    Research output: Chapter in Book/Report/Conference proceedingChapterpeer-review

    18 Citations (Scopus)

    Abstract

    The di-π-methane (DPM) rearrangement reaction is one of the most studied photochemical transformations. The oxa-di-π-methane (ODPM) rearrangement reaction has been recognized as a powerful synthetic protocol and one that can be applied to both cyclic and acyclic substrates. In the case of aza-di-π-methane (ADPM) rearrangement reactions involving 1-aza-1,4-dienes, regioselective conversions have been observed. The DPM reaction usually takes place through a singlet pathway (S1) in the excited state when acyclic 1,4-dienes are involved. The DPM rearrangement reaction requires a substrate incorporating two olefinic residues (π-systems) linked to a common sp3-hybridized carbon or, in other words, a 1,4-diene. A range of methods is available for the synthesis of the acyclic 1,4-dienes required as substrates for the DPM rearrangement reaction, and some of these are also summarized in the chapter.

    Original languageEnglish
    Title of host publicationMolecular Rearrangements in Organic Synthesis
    PublisherWiley
    Pages261-288
    Number of pages28
    ISBN (Electronic)9781118939901
    ISBN (Print)9781118347966
    DOIs
    Publication statusPublished - 12 Oct 2015

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