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

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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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http://eprints.maynoothuniversity.ie/7972/1/FH-Site-2001.pdf

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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