X = Y - ZH Systems as Potential 1,3-Dipoles. Part 37. Generation of Nitrones from Oximes. Tandem Intramolecular 1,3-Azaprotio Cyclotransfer - Intramolecular 1,3-Dipolar Cycloaddition Reactions. Class 4 Processes.

Article abstract of DOI:10.1016/S0040-4020(01)88344-7

Aldoximes and ketoximes containing two alkenyl moieties in different side chains undergo thermal conversion to 5- and 6-membered cyclic nitrones, via concerted 1,3-azaprotio cyclotransfer, followed by stereospecific intramolecular cycloaddition to give spiro- and fused-ring systems.An X-ray crystal structure of one such product is reported. Keywords: Nitrones, cycloaddition, intramolecular, oximes.