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


    Heaney, Frances and Kelly, Bronwyn M. and Bourke, Sharon and Rooney, Oliver and 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: https://doi.org/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
    URI:

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