Tetrahedron Letters p. 921 - 924 (1980)
Update date:2022-08-25
Topics:
Schleyer, Paul von Rague
Grubmueller, Peter
Maier, Wilhelm F.
Vostrowsky, Otto
Skatteboel, Lars
Holm, Kjetil H.
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).
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