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The Adamantane Rearrangement of Tricyclo[4.2.2.01,5]decane to Tricyclo[5.3.0.04,8]decane

✍ Scribed by Kanai L. Ghatak; Camille Ganter

Publisher
John Wiley and Sons
Year
1988
Tongue
German
Weight
345 KB
Volume
71
Category
Article
ISSN
0018-019X

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✦ Synopsis

Regioselective generation of the C(2)-carbocation a of tricyc10[4.2.2.0',~]decane (1) by treatment of both corresponding epimeric alcohols 5 and 6 with BF, and trapping the rearranged tricy~lo[S.3.0.O~~~]decan-7-yl carhocation b with Et,SiH 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).

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