Bridged compoundsBridged compounds Q 0060 Products of Reaction of Tricyclo[4.1.0.0 2,7 ]heptane and 1-Bromotricyclo[4.1.0.0 2,7 ]heptane with Hydrogen Sulfide, and Syntheses Based Thereon. -UV-irradiation of title tricycloheptane derivatives like (I) in the presence of hydrogen sulfide furnishes the corresponding thiols [cf. (II)] and sulfides [cf. (III)] with regioselective opening of the central C(1)-C(7) bond. In the presence of bromine substituent, the reaction proceeds with excellent stereoselectivity. Oxidation of the sulfide can be carried out selectively to give sulfoxides [cf. (IV)] or sulfones [cf. (VI)] in good yields. Dehydrobromination of these sulfoxides and sulfones provides access to the sulfoxides and sulfones of the tricycloheptane series. It is shown, however, that only bromine substituents in syn-position can be eliminated [cf. (VIII) vs. (IX)]. -(VASIN, V. A.; KOSTRYKOV, S. G.; RAZIN, V. V.; Russ. J. Org. Chem. 38 (2002) 11, 1582-1587; Ogarev Mordovian State Univ., Saransk 430000, Russia; Eng.) -Mischke 25-099 2003 Bridged compounds
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