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Date: 8-10-2020
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Date: 26-1-2020
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Osmium tetroxide oxidizes alkenes to give glycols through syn addition. A glycol, also known as a vicinal diol, is a compound with two -OH groups on adjacent carbons.
The reaction with OsO4 is a concerted process that has a cyclic intermediate and no rearrangements. Vicinal syn dihydroxylation complements the epoxide-hydrolysis sequence which constitutes an anti dihydroxylation of an alkene. When an alkene reacts with osmium tetroxide, stereocenters can form in the glycol product. Cis alkenes give meso products and trans alkenes give racemic mixtures.
OsO4 is formed slowly when osmium powder reacts with gasoues O2 at ambient temperature. Reaction of bulk solid requires heating to 400 °C:
Since Osmium tetroxide is expensive and highly toxic, the reaction with alkenes has been modified. Catalytic amounts of OsO4 and stoichiometric amounts of an oxidizing agent such as hydrogen peroxide are now used to eliminate some hazards. Also, an older reagent that was used instead of OsO4 was potassium permanganate, KMnO4. Although syn diols will result from the reaction of KMnO4 and an alkene, potassium permanganate is less useful since it gives poor yields of the product because of overoxidation.
Example: Dihydroxylation of 1-ethyl-1-cycloheptene
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