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

Authors
Heaney, F Kelly, BM Bourke, S Rooney, O Cunningham, D McArdle, P
Citation
F. Heaney et al., Site selectivity in the addition of ketoximes to activated allenes and alkynes; N- versus O-alkylation, J CHEM S P1, (2), 1999, pp. 143-148
Citations number
40
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Issue
2
Year of publication
1999
Pages
143 - 148
Database
ISI
SICI code
0300-922X(19990121):2<143:SSITAO>2.0.ZU;2-6
Abstract
Reaction of ketoximes with methyl propiolate afforded geometrical isomers o f the methyl 3-(hydroxyimino)propanoates 4 and of the O-vinyl oximes 5 as w ell 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 ca se of cyclopentanone oxime was the spirocyclic dihydroazepinol 11 also obta ined, its identity has been confirmed by an X-ray structure determination.