Nitrones. Part IX. The synthesis and reactions of 2,3-dihydro-1,4-oxazine 4-oxide, a heterocyclic nitrone

Abstract

Solutions in both chloroform and water of 4-hydroxymorpholine, when treated with a variety of oxidising agents, yielded 2,3-dihydro-1,4-oxazine 4-oxide (IV) as established by spectral and cycloaddition studies. When the solvent was removed, the heterocyclic nitrone (IV) yielded polymers, believed to have a chain-type structure (X). The nitrone (IV) behaved as a typical nitrone towards reducing agents. It was oxidised by arylhydrazines and by ferric chloride. With reactive π-bond systems it formed 1,3-cycloaddition products, the structures of which have been established by analysis and spectral data.