Six possible isomers resulting from the replacement of one or both benzene rings in 9,10-anthraquinone with thiophene rings have been synthesized: 4,9-dihydronaphtho[2,3-6]thiophene-4,9-dione (1), 4,9-dihydronaphtho-[2,3-c]thiophene-4,9-dione (2), 4,8-dihydrobenzo[l,2-6:5,4-b']dithiophene-4,8-dione (3), 4,8-dihydrobenzo[1,2-6:4,5-6']dithiophene-4,8-dione (4), 4,8-dihydrobenzo[l,2-6:4,5-c']dithiophene-4,8-dione (5), and 4,8-dihydrobenzo [1,2-c :4,5-c']dithiophene-4,8-dione (6). Compound 6 was prepared by dechlorination of 1,3-dichloro-4,8-dihydrobenzo[1,2-c:4,5-c']dithiophene-4,8-dione (15). The compounds 1, 2, 3, 4, 5, and 15 were subjected to reduction by means of an equimolar mixture of aluminum chloride-lithium aluminum hydride. Compounds 3 and 4 show only reduction to the hydroquinone stage. Compounds 2 and 15 provide good yields of the corresponding dihydroaromatic systems, while 1 and 5 afford only moderate yields of the dihydroaromatic systems. These results are explained in terms of the position of keto-enol tautomerism in the corresponding anthroneanthrol systems and the stability of the parent aromatic systems.