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

Patrick Mcardle

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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.
Original languageEnglish (Ireland)
Number of pages6
JournalJournal Of The Chemical Society-Perkin Transactions 1
Publication statusPublished - 1 Jan 1999

Authors (Note for portal: view the doc link for the full list of authors)

  • Authors
  • Heaney, F,Kelly, BM,Bourke, S,Rooney, O,Cunningham, D,McArdle, P

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