19026-94-9Relevant academic research and scientific papers
AN ADAMANTANE REARRANGEMENT. A NEW PATHWAY
Schleyer, Paul von Rague,Grubmueller, Peter,Maier, Wilhelm F.,Vostrowsky, Otto,Skatteboel, Lars,Holm, Kjetil H.
, p. 921 - 924 (1980)
Tricyclo(4.2.2.01,5)decane (7) in the presence of AlBr3 rearranges partly "forwards" to adamantane (1) and partly "backwards" to tetrahydrodicyclopentadiene (2, largely the exo isomer).Intermediate 14, characterizing the 7 exo-8 14 3 1 forward pathway, is found only in small amounts.The detection of a new intermediate, 12, also shows that a second major rearrangement route from 7 to 1 is being utilized (see dashed lines in Figure 1).
The Novel Adamantane Isomer Tricyclo3,9>decane (2-Homotwistbrendane)
Kaenel, Hans-Ruedi,Ganter, Camille
, p. 1226 - 1234 (2007/10/02)
Two synthetic approaches to the novel C10H16 hydrocarbon tricyclo3,9>decane (1; 2-homotwistbrendane), one of the 19 members of the adamantaneland, and its Lewis-acid-catalyzed rearrangement are described.One route starts from tricyclo3,8>nonan-2-one (2; 2-twistbrendanone).The missing tenth C-atom is introduced by ring enlargement (Tiffeneau-Demjanov method).Starting from methyl 8,9,10-trinorborn-5-ene-2-endo-carboxylate (8), ring enlargement by one C-atom, regio- and stereoselective introduction of a C1 unit to a 2-endo,6-endo-disubstituted bicyclo octane, and ring closure by acyloin condensation are the key steps in the second approach.
Diademane and Structurally Related Compounds, II. Catalytic Rearrangements and Hydrogenations
Kaufmann, Dieter,Schallner, Otto,Meyer, Lueder-Ulrich,Fick, Hans-Heinrich,Meijere, Armin de
, p. 1377 - 1385 (2007/10/02)
Copper, silver, gold, and rhodium compounds catalyze the rearrangement of diademane (1) to triquinacene (5) and snoutene (7), respectively.Known mechanism may be adopted to explain this behaviour.The catalytic hydrogenation of 1 leads to a mixture of 6 products, 9 - 14, the composition of which was independent of the extent of reaction.Adamantane, the thermodynamically most stable isomer of all conceivable "hexahydrodiademanes", was not detected.
