Journal of the Chemical Society. Perkin transactions I p. 800 - 806 (1973)
Update date:2022-08-03
Topics:
Oakland, John S.
Scheinmann, Feodor
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[4.2.1.03,7]nonane (32).
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