Studies in the norbornene series. Part II. Synthesis and reactions of some norbornanes carrying fused heterocycles

Abstract

Some norbornanes carrying fused heterocycles have been synthesised by 1,3-dipolar additions to substituted norbornenes. Attempts to prepare heterocycles by reactions of electrophilic reagents with the strained double bond in norbornenes were unsuccessful owing to the occurrence of rearrangements. In the reaction of iodine with 5-endo-aminomethylnorborn-2-ene, rearrangement may be prevented by prior nucleophilic attack of the amine group on the cation intermediate to give a 5-azatricyclo[4.2.1.0]nonane (32).