9-Alkoxy (or acyloxy)-10-methylanthracenes undergo reaction with cupric halides at the Me group to give coupled products, whereas 9-alkoxy (or acyloxy)-10-benzyl (or ethyl) anthracenes react at the alkoxy or acyloxy group to afford 10-benzyl-and 10- ethylideneanthrones respectively. Both types of reaction are postulated to proceed by a radical mechanism. 9-Benzyl-and 9-methyl-10-phenoxyanthracenes behave differently ...