Cyclic nitrone-ethene cycloaddition reactions

Addition reactions of ethene onto several cyclic nitrones afforded [n,3,0]heterobicyclicalkanes devoid of any substituents in the ring skeleton. These fused ring systems with a bridgehead nitrogen, capable of undergoing nitrogen inversion, allowed us to determine the stereochemistry of the ring fusion and the thermodynamic stability of the cis, trans isomers. Some of the cycloadducts on peracid induced ring opening gave a new series of nitrones capable undergoing further cycloaddition reactions.