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

dc.contributor.authorHeaney, Frances
dc.contributor.authorKelly, Bronwyn M.
dc.contributor.authorBourke, Sharon
dc.contributor.authorRooney, Oliver
dc.contributor.authorCunningham, Desmond
dc.contributor.authorMcArdle, Patrick
dc.date.accessioned2018-08-24T08:25:06Z
dc.date.available2018-08-24T08:25:06Z
dc.date.issued1999-01-01
dc.identifier.citationHeaney, 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
dc.identifier.issn0300-922X,1364-5463
dc.identifier.urihttp://hdl.handle.net/10379/9284
dc.description.abstractReaction 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.
dc.publisherRoyal Society of Chemistry (RSC)
dc.relation.ispartofJournal of the Chemical Society, Perkin Transactions 1
dc.rightsAttribution-NonCommercial-NoDerivs 3.0 Ireland
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/3.0/ie/
dc.subjectcyclization-cycloaddition reactions
dc.subjectx=y-zh systems
dc.subjectcyclic nitrones
dc.subjectalkenyl oximes
dc.subject1,3-azaprotio cyclotransfer
dc.subject1,3-dipolar cycloadditions
dc.subjectpotential 1,3-dipoles
dc.subjectring
dc.subjectdipolarophiles
dc.subjectpiperidines
dc.titleSite selectivity in the addition of ketoximes to activated allenes and alkynes; n- versus o-alkylation
dc.typeArticle
dc.identifier.doi10.1039/a808167k
dc.local.publishedsourcehttp://eprints.maynoothuniversity.ie/7972/1/FH-Site-2001.pdf
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