AN ADAMANTANE REARRANGEMENT. A NEW PATHWAY

Article abstract of DOI:10.1016/S0040-4039(00)77739-2

Tricyclo(4.2.2.0^1,5)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).