Dual Reactivity in 1,2-Disubstituted Dihydro-N-heteroaromatic Systems. 12. Aromatization of 1-Substituted-2-(indol-3-yl)-1,2-dihydroquinolines with 1,3,5-Trinitrobenzene

Article abstract of DOI:10.1007/BF00475571

As the electron-acceptor properties of the N-substituents in 1-R-2-(indol-3-yl)-1,2-dihydroquinolines decrease, their ability to undergo heterolysis of the internuclear C-C bond to give ion pairs of 1-R-quinolinium cations and indole anions decreases.Reaction of these ion pairs with 1,3,5-trinitrobenzene gives salts of 1-R-quinolinium cations and the 1-(indol-3-yl)-2,4,6-trinitrocyclohexadiene anion.With undissociated dihydroquinolines, aromatization under similar conditions gives salts of 1-R-2(indol-3-yl)quinolinium cations and the 1,1-dihydro-2,4,6-trinitrocyclohexa diene anion.