By Patrick S. Mariano

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The (aminopropyl)phenanthrene 115 yields a mixture of the phenanthropiperidines 117 and 118, which are also formed via nucleophilic addition to form a sixmembered ring. An alternate approach to ET-sensitized intramolecular areneamine addition is being explored by Jung and Mariano. ~ CH3CN 119 O 120 a-silylamide 119 in acetonitrile solution affords the adduct 120. In this reaction, the silylamide serves as the precursor of an ct-amido radical intermediate which adds to the phenanthrene. Reduction of the resulting ot-keto radical and stereoselective protonation yields the adduct 120.

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