Multiple Dissolving-Metal Reduction of Centropolyindans: Synthesis of a Hexakis(cyclohexano)centrohexaquinacene

Eckrich R, Kuck D. Multiple Dissolving-Metal Reduction of Centropolyindans: Synthesis of a Hexakis(cyclohexano)centrohexaquinacene. Synlett. 1993;1993(05):344-347.Four prototype centropolyindans 1, 3, 7, and 10 were subjected to reduction with Li/NH3 and Li/NH2Me. While Birch reduction of 1, 3, and 7 gives medium to good yields of the corresponding two-, three-, and sixfold 1,4-cyclohexadienes 2, 4, and 8, respectively, centrohexaindan 10 does not react at all. With Li in NH2Me, however, 10 is converted to the corresponding hexaene, the title compound 12. Similarly, Benkeser reductions of 1 and 7 give the corresponding triquinacene 6 and the [3.3.3]propellatriene 9. Preliminary epoxidation and hydrogenation experiments of some polycyclic olefins are presented