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

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Date
1999-01-01
Author
Heaney, Frances
Kelly, Bronwyn M.
Bourke, Sharon
Rooney, Oliver
Cunningham, Desmond
McArdle, Patrick
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Heaney, Frances; Kelly, Bronwyn M. Bourke, Sharon; Rooney, Oliver; Cunningham, Desmond; 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 (2), 143-148
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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.
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http://hdl.handle.net/10379/9284
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