The stereochemistry and reactivity of the cycloaddition reactions of eight-membered cyclic nitrone (4) with several alkenes have been studied. The concentrated solution of the cyclic nitrone undergoes polymerization to give acyclic polynitrone (15). The nitrone 4 is found to be less reactive than its seven-membered counterpart. Barrier to nitrogen inversion in one of the cycloaddition product, a 8 5 fused ring system, was determined to be 55.4 kJ/mol.
