10.1021/jo00299a031
The research aimed to synthesize pentaleno[2,1-b:5,4-b']diindoles, which are complex organic compounds, using a combination of the Weiss reaction and the Fischer indole cyclization. The purpose was to prepare hexahydro-5,11-dihydropentaleno[2,1-b:5,4-b']diindoles and convert them into various 6,12-disubstituted derivatives. Despite numerous attempts, the researchers were unable to successfully convert these intermediates into bis(indo1o-substituted)pentalenes 5 or 6, as all attempts resulted in decomposition or ring scission products. The chemicals used in this process included phenylhydrazine, hydrochloric acid, selenium dioxide, phenylselenol, zinc iodide, and various solvents and reagents for chromatography and spectroscopic analysis. The conclusions drawn from the research were that while the diindole perhydropentalenes could be synthesized, the stabilization provided by the indole units in the targeted pentalenes was insufficient to prevent decomposition, suggesting that the benzene rings in dibenzopentalenes offer more effective stabilization than the indole units.