Heaney, Frances and Kelly, Bronwyn M. and Bourke, Sharon and Rooney, Oliver and 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
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: |
https://doi.org/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 |
| URI: |
|
| 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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