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

Author

Feodor Scheinmann and John S. Oakland

Subjects
chemistry.chemical_classification, chemistry.chemical_compound, Double bond, chemistry, Nucleophile, Reagent, Electrophile, Organic chemistry, Amine gas treating, Nonane, Medicinal chemistry, Norbornene
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).

Published
1973

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