Halogen-induced formation of nitrones from oximes and alkenes

Abstract

Oximes possessing γ-, δ-, or ω-alkenyl substituents are cyclised by N-bromosuccinimide or iodine to the corresponding cyclic nitrones or their dimeric H-bonded hydriodide salts in good yield; facially specific cycloaddition of these nitrones, and others derived by cyclisation of a δ,δ-bis(alkenyl) ketoxime or addition of acetaldoxime to cyclohexene, furnish isoxazolidines.