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 |
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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://mu.eprints-hosting.org/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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