A Novel Nitrone Cycloaddition/Rearrangement

Adamantanone-derived nitrone 4 and some other keto-nitrones, when reacted with aromatic and aliphatic aldehydes in refluxing toluene or tetrahydrofuran, formed the corresponding aldonitrones (Z)- 10 , the latter arising from the fragmentation of an initially formed 1 , 4 , 2 -dioxazolidine 6 to adamantan-2-one and an oxaziridine intermediate 11 , which then rearranges to (Z)- 10 .