The endo‐ and exo‐alcohols 5–12 of syn‐(1) and anti‐tricyclo[4.2.1. 12.5]decane (2) were treated with BF3/Et3SiH (ionic hydrogenation) in order to study the behaviour of the corresponding regioselectively generated carbocations at C(3) (a (syn), b (anti)) and C(9) (c (syn), d (anti)). The anti‐hydrocarbon 2 is practically the sole product obtained starting with the four 3‐alcohols (via a→b from 5 and 6 (syn) and via b from 9 and 10 (anti)). The four 9‐alcohols in each case yield a mixture of 2‐endo, 3‐endo‐ (3) and 2‐exo,3‐exo‐trimethylene‐8,9,10‐trinorbornane (4) (via c → e from 7 and 8 (syn) and via d → f from 11 and 12 (anti)), but no hydrocarbon 2, i.e. none of the 1,3‐H shifts c → a and d → b is involved.
ChemInform Abstract Treatment of the exo-alcohol (I) with BF3/Et3SiH (ionic hydrogenation) gives the anti-hydrocarbon (II) as virtually the sole product which is likewise obtained from the endo-alcohol (III) under the same conditions. In addition, (III) is obtained from the alcohols (IVa) or (IVb). On the other hand, the exo/endo alcohols (V) or (VIII) each afford a mixture of the 2-endo-3-endo-(VI) and 2-exo-3-exo-trimethylene-8,9,10-trinorbornanes (VII). Similar results are obtained from the alcohols (IXa) or (IXb). The mechanisms which govern the outcome of these reactions are discussed in detail.
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