Derivatives of 2,3-benzo-1-azabicyclo[2•2•1]hept-2-ene

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Abstract
2,3-Benzo-1-azabicyclo[2•2•1]hept-2-ene derivatives have been prepared by the introduction of a two-carbon bridge between positions-1 and -3 of the indole ring in 2,3-dimethylindole and tetrahydrocarbazole. In the former case both C-7 epimers were isolated and identified, and their nuclear magnetic resonance spectra were analyzed in detail. In the tetrahydrocarbazole series only one product was obtained and some ambiguity remains concerning the stereochemistry of this material. The physical properties of these compounds are of interest because the lone pair electrons on nitrogen are not able to overlap with the aromatic π system; the chemical properties are characterized by a facile cleavage of the tertiary amine under acylating conditions.

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