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Heating 1-vinyl-4,5,6,7-tetrahydro-5-methyl-4,6-ethanopyrrolo(3,2-c)pyridine (1) in the presence of acetic or trifluoroacetic anhydride resulted in bicyclic saturated fragment cleavage, affording cyclohepteno(b)pyrroles 2a,b in low yields. In the case of trifluoroacetic anhydride, the major product of the reaction, -trifluoroacetylsubstituted tetrahydropyrrolo(3,2-c)pyridine 3 was isolated in 34% yield.

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Unusual transformations of 1-vinyl-4,5,6,7-tetrahydro-5-methyl-4,6-ethanopyrrolo[3,2-c]pyridine to cyclohepteno[b]pyrroles under acetylation conditions