Octet / Reactions
Syn Dihydroxylation (OsO₄)
Syn Dihydroxylation (OsO₄) (Addition.) Converts CC=CC to CC(O)C(O)C using OsO₄, cat. OsO₄ with NMO. Stereochemistry: Syn addition (both OHs on same face).
Addition
Reaction details
Name
Syn Dihydroxylation (OsO₄)
Type
Addition
Starting Material
CC=CC
Product
CC(O)C(O)C
Reagents
OsO₄
cat. OsO₄ with NMO
Mechanism
- Smiles
CC=CC
- Description
2-Butene
- Smiles
CC1OOsO2OC1C
- Description
Cyclic osmate ester forms (concerted)
- Smiles
CC(O)C(O)C
- Description
Hydrolysis gives syn-diol
Stereochemistry
Syn addition (both OHs on same face)
Tips
OsO₄ is toxic and expensive - use catalytic with NMO
Alternative: cold, dilute KMnO₄ (also syn)
Related Reactions
dihydroxylation-anti
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