Peer-Reviewed Journal Details
Mandatory Fields
Doyle L.;Heaney F.
2010
August
Tetrahedron
An investigation of structure-reactivity relationships of δ-alkenyl oximes; Competitive thermal reactions leading to cyclic nitrones and/or N-unsubstituted bicyclic isoxazolidines
Published
()
Optional Fields
Azaprotio Cyclotransfer (APT) Intramolecular oxime olefin cycloaddition (IOOC) N-Unsubstituted isoxazolidines Oxime geometry
66
34
7041
7049
Thermal reactions of C-aryl δ-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. The nature of the aryl group, oxime geometry, and the structure of the linker between the oxime and the alkene influence the reactivity of C-aryl δ-alkenyl oximes. © 2010 Elsevier Ltd. All rights reserved.
0040-4020
10.1016/j.tet.2010.06.005
Grant Details