Volume 19, Issue 4
Preparative Organic Chemistry
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ChemInform Abstract: The Aluminum-Bromide-Catalyzed Adamantane Rearrangement of syn- and anti-Tricyclo(4.2.1.12,5)decane.

M. BROSSI

M. BROSSI

Lab. Org. Chem., ETH, ETH-Zent., CH-8092 Zuerich

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C. GANTER

C. GANTER

Lab. Org. Chem., ETH, ETH-Zent., CH-8092 Zuerich

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First published: January 26, 1988

Abstract

In the presence of AlBr3 in CS2 at temperatures below 0 °C, the syn-tricyclodecane (I) isomerizes exclusively to the anti-isomer (II) at a higher rate than the latter rearranges to (III).

ChemInform Abstract

In the presence of AlBr3 in CS2 at temperatures below 0 °C, the syn-tricyclodecane (I) isomerizes exclusively to the anti-isomer (II) at a higher rate than the latter rearranges to (III). However, at temperatures above 0 °C, the anti-isomer (II) isomerizes to (III) faster than (I) to (II) and (III). The structures and reactivities of the intermediate carbocations are discussed.

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