MURAL - Maynooth University Research Archive Library



    Steric control of reactivity: formation of oximes, benzodiazepinone N-oxides and isoxazoloquinolinones


    Heaney, Frances and Bourke, Sharon and Cunningham, Desmond and McArdle, Patrick (1998) Steric control of reactivity: formation of oximes, benzodiazepinone N-oxides and isoxazoloquinolinones. Journal of the Chemical Society, Perkin Transactions 2, 1998 (3). pp. 547-560. ISSN 1472-779X

    [img]
    Preview
    Download (187kB) | Preview


    Share your research

    Twitter Facebook LinkedIn GooglePlus Email more...



    Add this article to your Mendeley library


    Abstract

    Reaction of the alkenyl carbonyl compounds 1 with hydroxylamine can lead to the formation of the oximes 2, the benzodiazepinone N-oxides 3 or the isoxazoloquinolinones 5. The product(s) of reaction are shown to depend on the electronic nature of the terminal olefinic substituent R3 and the space filling capacity of the substituents R1, R2 and R4. When the olefinic centre is electron poor (R3 = CO2Et) ketocarbonyls convert exclusively to bicyclic nitrones 3 whereas aldehydes are more sensitive to subtle changes in skeletal structure and give rise to oximes 2, tricycles 5 or mixtures of both. For aldehyde and ketone substrates when the olefinic centre carries an aryl substituent (R3 = Ph) the primary product of reaction is the corresponding oxime which on thermal activation converts to the tricyclic isoxazoloquinolinones.

    Item Type: Article
    Keywords: Steric control; reactivity; oximes; benzodiazepinone N-oxides; isoxazoloquinolinones;
    Academic Unit: Faculty of Science and Engineering > Chemistry
    Item ID: 7971
    Identification Number: https://doi.org/10.1039/A707857I
    Depositing User: Dr. Frances Heaney
    Date Deposited: 24 Feb 2017 16:30
    Journal or Publication Title: Journal of the Chemical Society, Perkin Transactions 2
    Publisher: Royal Society of Chemistry
    Refereed: Yes
    Funders: Eolas, Mayo County Council
    URI:

    Repository Staff Only(login required)

    View Item Item control page

    Downloads

    Downloads per month over past year