ChemInform Abstract: The Aluminum-Bromide-Catalyzed Adamantane Rearrangement of syn- and anti-Tricyclo(4.2.1.12,5)decane.
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.