Mechanisms of hydrogenation. Part X. Homogeneous hydrogenolysis of organic halides and hydrogenation of the carbonyl, epoxy-, and nitro-groups
- 1 January 1973
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 2509-2512
- https://doi.org/10.1039/p19730002509
Abstract
The catalyst formed from trichlorotris(pyridine)rhodium with sodium borohydride in dimethylformamide is shown to be effective for the homogeneous hydrogenolysis of the carbon–halogen bond, R–X, where R = benzyl, allyl, aryl, or –CO–C but not alkyl, and X = Cl or Br. Vicinal dihalides have also been hydrogenolysed. The stereochemistry of halogen displacement is consistent with a free-radical mechanism. The carbonyl groups in acetophenone, benzophenone, and benzoin have been hydrogenated with this catalyst system, and styrene oxide gives 2-phenylethanol. Examples of hydrogenation of nitro-groups (RNO2→ RNH2; R = aryl or cyclohexyl) are reported.Keywords
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