| Abstract: | The interaction of phenalenonc and 2-methylindole in presence of stoechiomctric amounts of paratoluenesulfonic acid in methanol under argon, yields twelve compounds which have been spectroscopically characterised. Seven compounds or sets of compounds could be scpareted by flash chromatography. Phenalene 4. and phenalanone 8 result from a disproportionalion reaction of a key intermediate 18. 2-Methylindolylphenalene 5 and bis(2-methyl)indolylphenalene 6 and 7 exist under the form of a complex mixture of lauiomers. 2-Methylindolylphenalanones 9 and 10. 2-methylindolylphenalenones 11. 12. 1 3. and bis(2-methylindolyl)phenalenones 14 and 15. could also be isolated from the reaction mixture. In presence of air and light compounds 5, 6, and 7. oxidize into 11, 12, 13, 14, and 15 via the corresponding phenalenyl radical. The mechanism of formation and interconversion of these products is discussed and experimentally supported. The peculiar reactivity of the phenalenic derivatives is analysed and it is suggested that such structures are present in asphaltenes. An hypothesis about their genesis is proposed. |
