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Heaney, Frances, Kelly, Bronwyn M., Bourke, Sharon, Rooney, Oliver, Cunningham, Desmond and 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, 1. pp. 143-148. ISSN 0300-922X
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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.
| Item Type: | Article |
|---|---|
| Keywords: | Site selectivity; ketoximes; activated allenes; alkynes; N- versus O-alkylation; |
| Academic Unit: | Faculty of Science and Engineering > Chemistry |
| Item ID: | 7972 |
| Identification Number: | 10.1039/A808167K |
| Depositing User: | Dr. Frances Heaney |
| Date Deposited: | 24 Feb 2017 16:29 |
| Journal or Publication Title: | Journal of the Chemical Society, Perkin Transactions 1 |
| Publisher: | Royal Society of Chemistry |
| Refereed: | Yes |
| Funders: | Forbairt |
| Related URLs: | |
| URI: | https://mural.maynoothuniversity.ie/id/eprint/7972 |
| Use Licence: | This item is available under a Creative Commons Attribution Non Commercial Share Alike Licence (CC BY-NC-SA). Details of this licence are available here |
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