Homolytic replacement of a hydrogen atom in 2-methylquinoline by A 1,3-dioxolanyl residue
The reaction of 1,3-dioxolane with sulfuric-acid-protonated 2-methylquinoline initiated by the ROOH + Fe2+ system [where R = H, (CH3)3C, or C6H5C(CH3)2] at 5–10 °C in water forms 4-(1,3-dioxacyclopent-2-yl)-2-methylquinoline and 4-(1,3-dioxacy-clopent-4-yl)-2-methylquinoline. The selectivity of the formation of the first reaction product increases on passing from hydrogen peroxide to cumyl and tert-butyl hydroperoxide and with an increase in the pH of the medium.