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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
; 
McArdle, Patrick
Identifiers
http://hdl.handle.net/10379/9284
https://doi.org/10.13025/24186
Repository DOI
10.1039/a808167k
Publication Date
1999-01-01
Keywords
cyclization-cycloaddition reactions, x=y-zh systems, cyclic nitrones, alkenyl oximes, 1,3-azaprotio cyclotransfer, 1,3-dipolar cycloadditions, potential 1,3-dipoles, ring, dipolarophiles, piperidines
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Article
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Citation
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
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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Publisher
Royal Society of Chemistry (RSC)
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Rights
Attribution-NonCommercial-NoDerivs 3.0 Ireland
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Externally hosted open access publications with University of Galway authors (1)