14. The Adamantane Rearrangement of Tricyclo1,5>decane to Tricyclo4,8>decane

Article abstract of DOI:10.1002/hlca.19880710115

Regioselective generation of the C(2)-carbocation a of tricyclo<4.2.2.0^1,5>decane (1) by treatment of both corresponding epimeric alcohols 5 and 6 with BF3 and trapping the rearranged tricyclo<5.3.0.0^4,8>decan-7-yl carbocation b with Et3SiH as hydride-ion donor (ionic hydrogenation) gives the corresponding hydrocarbon 3 as sole product in almost quantitative yield.The latter is a known intermediate in the Lewis-acid-catalyzed rearrangement of 1 to adamantane (4).