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Issue 2, 1999
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Site selectivity in the addition of ketoximes to activated allenes and alkynes; N- versusO-alkylation

Frances Heaney,  Bronwyn M. Kelly,  Sharon Bourke,  Oliver Rooney,  Desmond Cunningham  and  Patrick McArdle 

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.

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Article type: Paper
DOI: 10.1039/A808167K
Citation: J. Chem. Soc., Perkin Trans. 1, 1999,0, 143-148
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    Site selectivity in the addition of ketoximes to activated allenes and alkynes; N- versusO-alkylation

    F. Heaney, B. M. Kelly, S. Bourke, O. Rooney, D. Cunningham and P. McArdle, J. Chem. Soc., Perkin Trans. 1, 1999, 0, 143
    DOI: 10.1039/A808167K

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