Octet / Reactions
Anti Dihydroxylation (Epoxide Opening)
Anti Dihydroxylation (Epoxide Opening) (Addition.) Converts CC1OC1C to CC(O)C(O)C using H₃O⁺/H₂O, or NaOH/H₂O. Stereochemistry: Anti addition (OHs on opposite faces).
Addition
Reaction details
Name
Anti Dihydroxylation (Epoxide Opening)
Type
Addition
Starting Material
CC1OC1C
Product
CC(O)C(O)C
Reagents
H₃O⁺/H₂O
or NaOH/H₂O
Mechanism
- Smiles
CC1OC1C
- Description
Epoxide
- Smiles
CC(O)C(O)C
- Description
Ring opening with water gives anti-diol
Stereochemistry
Anti addition (OHs on opposite faces)
Tips
Acid-catalyzed: opens at more substituted carbon
Base-catalyzed: opens at less substituted carbon
Related Reactions
dihydroxylation-syn
epoxidation
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