Mercuric acetate induced formation of cyclic nitrones from alkenyl oximes

Abstract

Oximes possessing γ- or δ-alkenyl substituents are cyclised by mercuric acetate to the corresponding cyclic nitrones; the mercurated nitrones undergo facially specific cycloaddition reactions with N-methylmaleimide to afford endo- and exo-cycloadducts, δ,δ--bis(alkenyl) ketones undergo stereospecific cyclisation–intramolecular cycloaddition to furnish spirocyclic products.