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Abstract
The hydrogenation of non-migrating double bonds in bicyclic olefins over platinum, palladium, and rhodium was investigated. With platinum, up to 16% antarafacial ( trans) addition was observed. The hydrogenation over palladium proceeded suprafacially ( cis) in neutral medium, but in the presence of strong acid up to 60% antarafacial addition accured. Hydrogenation over rhodium gave almost exclusively suprafacial addition in neutral or acidic medium. The antarafacial reaction was investigated by means of tracer experiments with deuterium. The antarafacial addition of hydrogen in the presence of palladium in acidic medium is caused by participation of the protonated solvent.
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