The reaction of iodine with 9-methylacridine: formation of polyiodide salts and a charge-transfer complex
Rimmer, E. L.; Bailey, R. D.; Pennington, W. T.; Hanks, T. W. The reaction of iodine with 9-methylacridine: formation of polyiodide salts and a charge-transfer complex. J. Chem. Soc. , Perkin Trans. 2 (1972-1999) 1998, 2557-2562.
The reaction of iodine and 9-methylacridine in methylene chloride results not in the formation of a charge-transfer complex as with acridine, but in the iodine-rich salt ICH2C13H8N-“H]4(I8)(I5)2, 8, where a proton on the methyl group has been replaced by an iodine. In toluene, the reaction produces both a charge-transfer complex ICH2C13H8N-“I2, 9, and a salt CH3-“acridine(H)]2(I7)(I5), 10. Polyiodide salt formation can be explained by the availability of a facile reaction pathway from the aryl radical cation which results from initial oxidation by I2.
Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999)