The readily available e«do-7-aminomethylbicyclo[3.3.1]nonan-3-one serves as a convenient precursor for a variety of 3-and 3,7-substituted bicyclo[3.3.1]nonanes. The individual steps generally proceed in high yield.New compounds which are made available include endo-3-bicyclo[3.3.1] nonylmethylamine, iV,jV-dimethyl-7methylene-endo -3-bicyclo [3.3.1] nonylamine, 7-methylenebicyclo [3.3.1] non-2-ene, and endo-3-bicyclo [3.3.1]nonylcarbonitrile. l-Methyl-2-oxaadamantane was also prepared. In addition, novel routes are provided for the indicated substances, 3-methylenebicyclo [3.3.1] nonane, endo-3-methylbicyclo [3.3.1] nonane, 3-methylbicyclo- [3.3.1] non-2-ene, and 3-bicyclo[3.3.l]nonylcarboxylic acid.Various methods have been employed for the preparation of bicyclo [3.3.1 [nonanes, in which acyclic or monocyclic materials serve as the immediate precrusors.2 Included in some of the newer approaches is the ring opening of suitably substituted adamantanes, which generally leads to 3,7-disubstituted derivatives.2•3 Recently, in this category, l-V,V-dichloroaminoadamantane was found4 to provide endo-7-aminomethylbicyclo[3.3.1]nonan-3-one (1) in good yield from rearrangement by aluminum chloride with subsequent
Das Keto‐amin (I) liefert nach Wolff‐Kishner das Amin (II), das über das Dimethylamin (III) und das Ammoniumsalz (IV) zum Methylen‐Derivat (V) reagiert und weiter zum 3‐Methyl‐bicyclo(3,3,l)nonan (VI) hydriert wird.
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