Helvetica Chimica Acta p. 1963 - 1966 (1987)
Update date:2022-08-05
Topics:
Brossi, Marco
Ganter, Camille
In the presence of AlBr3 in CS2 at temperatures below 0 deg C, syn-tricyclo<4.2.1.12,5>decane (1) isomerizes exclusively to anti-tricyclo<4.2.1.12,5>decane (2) at a higher rate than the latter rearranges to 2-exo,3-exo-trimethylene-8,9,10-trinorbornane (4).However, at temperatures above 0 deg C, the anti isomer 2 isomerizes to 4 faster than 1 to 2 and 4.As a consequence, hydride abstraction occurs at C(3) (->carbocation a, which rearranges to carbocation b (anti skeleton)) in the syn-isomer 1 and more readily at C(9) (->carbocation c) than at C(3) (->carbocation b) in the anti-isomer 2.
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