Double peri interactions of the C-9 methyl group in 1,4,5,8,9-pentamethylanthracene lead to a variety of reactions under mild conditions, all of which result in destruction of aromaticity in the central ring; this loss is more than compensated for by strain relief.
H. Hart and H. Wachi, J. Chem. Soc., Chem. Commun., 1977, 409 DOI: 10.1039/C39770000409
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