Regioselectivity of the bromination of 1-oxo-1,2,3,4-tetrahydronaphthalene and 6,7-dimethyl-1-oxo-1,2,3,4-tetrahydronaphthalene, and thiabiscyclanones synthesis on their basis

On the basis of quantum chemical (PM3 and RHF/6-31G*) study, the regioselectivity of the bromination of 1-oxo-1,2,3,4-tetrahydronaphthalene (1) and 6,7-dimethyl-1-oxo-1,2,3,4-tetra-hydronaphthalene (2) at their alicyclic and aromatic fragments was quantum chemically substantiated and confirmed experimentally. It was found that the above compounds undergo aromatic at the alpha-methylene positions. The conditions for bromination at the positions, 5, 8 of benzannelated ring were established. For the first time, non- and 2,2'-dibromosubstituted with respect to the oxo group bis(6,7-dimethyl-1-oxo-1,2,3,4-tetrahydronaphth-2-yl) sulphides (7, 8a, b) were obtained. The latter were found to show promise as stabilizing agents for the storage of cholera sera.