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An investigation of structure-reactivity relationships of d-alkenyl oximes; competitive thermal reactions leading to cyclic nitrones and/or N-unsubstituted bicyclic isoxazolidines
Doyle, Linda; Heaney, Frances
Thermal reactions of C-aryl d-alkenyl oximes give N-unsubstituted bicylic lactone, lactam and pyrrolidine fused isoxazolidines by an intramolecular oxime olefin cycloaddition pathway (IOOC) and/or cyclic nitrones by an azaprotio cyclotransfer (APT) route; a number of factors, including the nature of the aryl group, the oxime geometry and the structure of the linker between the oxime and the terminal alkene, contribute to the competition.
Keyword(s): Chemistry; N-Unsubstituted isoxazolidines; Oxime geometry; Intramolecular oxime olefin cycloaddition; (IOOC); azaprotio Cyclotransfer (APT)
Publication Date:
2010
Type: Journal article
Peer-Reviewed: Yes
Institution: Maynooth University
Citation(s): Doyle, Linda and Heaney, Frances (2010) An investigation of structure-reactivity relationships of d-alkenyl oximes; competitive thermal reactions leading to cyclic nitrones and/or N-unsubstituted bicyclic isoxazolidines. Tetrahedron, 66. pp. 7041-7049. ISSN 0040-4020
Publisher(s): Elsevier
File Format(s): application/pdf
Related Link(s): http://eprints.maynoothuniversity.ie/4290/1/FH_investigation.pdf
First Indexed: 2014-09-20 05:02:07 Last Updated: 2014-09-20 05:02:07