Learn about OsO4 Syn Dihydroxylation and its Mechanism of Action for Alkenes

OsO4 adds?

loss of CO2 (i.e. decarboxylation)

OsO4 (osmium tetroxide) adds via syn dihydroxylation reaction. This means that OsO4 adds two hydroxyl groups (-OH) to the double bond of an alkene, forming a vicinal diol. The reaction occurs in the presence of a suitable solvent such as acetone or tetrahydrofuran (THF) and usually requires the use of a co-oxidant like NMO (N-methylmorpholine N-oxide). This reaction is highly stereospecific and yields a cis-diol product. The mechanism of OsO4 addition involves the formation of a cyclic osmate ester intermediate, which subsequently undergoes hydrolysis to yield the diol product.

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