Accelerating Ligands for Osmium Tetraoxide Catalyzed Racemic Dihydroxylation of α-Pinene

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• In the osmium tetraoxide catalyzed TMO oxidation of cyclohexene, the rate is decreased by tert-amine ligands.11,12 An explanation for the ligand-accelerated or-decelerated osmium tetraoxide catalyzed oxidation of alkenes depending on the oxidation mechanisms of unhindred and sterically hindered alkenes has been given.2e,11
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• Osmium tetraoxide puchased in 500 mg ampules was used. To perapare 4% aqueous solution, one ampul is broken open and the two halves are dropped into a brown bottle containing 12.5 mL of water. The bottle is capped with a rubber septum and following complete dissolution of osmium tetraoxide, it is purged with a stream of nitrogen quickly. Each mililiter of this stock solution contains 0.040 g (0.157 mmol) of osmium tetraoxide.
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• The progress of the reaction was monitored by GC on a SE-30 column at 110°C. To obtain optimum results, one should follow the reaction by GC since longer heating of the reaction mixture reduces the yield and produces α-hydroxyketone.
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