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    Synthesis, structure and pyrolysis of stabilised phosphonium ylides containing saturated oxygen heterocycles

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    Open Access article (746.1Kb)
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    Publication date
    2016-04
    Author
    Aitken, R.A.
    Karodia, Nazira
    McCarron, H.B.
    Rouxel, C.
    Sahabo, Nina Carole
    Slawin, A.M.Z.
    Keyword
    Stabilised phosphonium ylides; Saturated oxygen heterocycles; Alkyne synthesis
    Rights
    © 2016 The Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
    Peer-Reviewed
    yes
    
    Metadata
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    Abstract
    A range of twelve stabilised phosphonium ylides containing tetrahydrofuran, tetrahydropyran or 2,2- dimethyl-1,3-dioxolane rings have been prepared and fully characterised, including one X-ray structure determination of each type. The X-ray structures confirm the PvC and CvO functions to be syn and all the compounds undergo thermal extrusion of Ph3PO to give the corresponding alkynes. In some cases there is also competing loss of Ph3P to give different carbene-derived products and evidence has been obtained for the generation of 2-phenyloxete in this way. Raising the pyrolysis temperature leads in several cases to new secondary reactions of the alkyne products involving a sequence of alkyne to vinylidene isomerisation, intramolecular CH insertion, and retro Diels Alder reaction.
    URI
    http://hdl.handle.net/10454/8426
    Version
    published version paper
    Citation
    Aitken RA, Karodia N, McCarron HB, Rouxel C, Sahabo N and Slawina AMZ (2016) Synthesis, structure and pyrolysis of stabilised phosphonium ylides containing saturated oxygen heterocycles. Organic & Biomolecular Chemistry. 14: 1794-1804.
    Link to publisher’s version
    http://dx.doi.org/10.1039/C5OB02467F
    Type
    Article
    Collections
    Life Sciences Publications

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