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  • Rearrangement of a Mesylate Tropane Intermediate inNucleophilic Substitution Reactions. Synthesis ofAza-Bicyclo[3.2.1]octane and Aza-Bicyclo[3.2.2]nonane Ethers,Imides, and Amines
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  • Nucleophilic substitution of 2β-mesyloxymethyl-N-methyl-3β-p-tolyl-tropane intermediate withalkoxides, metal imides, or amines was found to lead not only to the expected bicyclo[3.2.1]octane(tropane) ether, imide, and amine derivatives but also to unexpected bicyclo[3.2.2]nonane derivatives.When alkoxides were used as nucleophile, only the rearranged bicyclo[3.2.2]nonane structure wasobtained, whereas the use of amines or imides as nucleophile afforded a mixture of the twostructures. The bicyclo[3.2.2]nonane structure was assigned by NMR analysis.
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