An investigation of structure-reactivity relationships of d-alkenyl oximes; competitive thermal reactions leading to cyclic nitrones and/or N-unsubstituted bicyclic isoxazolidines

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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

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Abstract

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.

Item Type:	Article
Keywords:	N-Unsubstituted isoxazolidines; Oxime geometry; Intramolecular oxime olefin cycloaddition; (IOOC); azaprotio Cyclotransfer (APT);
Academic Unit:	Faculty of Science and Engineering > Chemistry
Item ID:	4290
Depositing User:	Dr. Frances Heaney
Date Deposited:	09 Apr 2013 09:12
Journal or Publication Title:	Tetrahedron
Publisher:	Elsevier
Refereed:	Yes
Related URLs:	Publisher
URI:	https://mu.eprints-hosting.org/id/eprint/4290
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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An investigation of structure-reactivity relationships of d-alkenyl oximes; competitive thermal reactions leading to cyclic nitrones and/or N-unsubstituted bicyclic isoxazolidines

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