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    Site selectivity in the addition of ketoximes to activated allenes and alkynes; N- versus O-alkylation


    Heaney, Frances, Kelly, Bronwyn M., Bourke, Sharon, Rooney, Oliver, Cunningham, Desmond and McArdle, Patrick (1999) Site selectivity in the addition of ketoximes to activated allenes and alkynes; N- versus O-alkylation. Journal of the Chemical Society, Perkin Transactions 1, 1. pp. 143-148. ISSN 0300-922X

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    Abstract

    Reaction of ketoximes with methyl propiolate afforded geometrical isomers of the methyl 3-(hydroxyimino)propanoates 4 and of the O-vinyl oximes 5 as well as the 2-isoxazoline 6. With dimethyl penta-2,3-diendioate 8c reaction progressed via an O-alkylation to give the O-oxime ethers 9, only in the case of cyclopentanone oxime was the spirocyclic dihydroazepinol 11 also obtained, its identity has been confirmed by an X-ray structure determination.
    Item Type: Article
    Keywords: Site selectivity; ketoximes; activated allenes; alkynes; N- versus O-alkylation;
    Academic Unit: Faculty of Science and Engineering > Chemistry
    Item ID: 7972
    Identification Number: 10.1039/A808167K
    Depositing User: Dr. Frances Heaney
    Date Deposited: 24 Feb 2017 16:29
    Journal or Publication Title: Journal of the Chemical Society, Perkin Transactions 1
    Publisher: Royal Society of Chemistry
    Refereed: Yes
    Funders: Forbairt
    Related URLs:
    URI: https://mu.eprints-hosting.org/id/eprint/7972
    Use Licence: This item is available under a Creative Commons Attribution Non Commercial Share Alike Licence (CC BY-NC-SA). Details of this licence are available here

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