Octet / Reactions
Mitsunobu Reaction
Mitsunobu Reaction (Substitution). Starts from Secondary alcohol with DEAD or DIAD, PPh₃, Nucleophile (pKa < 15). Stereochemistry: Inversion of configuration (like SN2). Mechanism in 3 steps.
Substitution
Reaction details
Name
Mitsunobu Reaction
Type
Substitution
Starting Material
CC(C)O
Product
CC(C)N3
Reagents
DEAD or DIAD
PPh₃
Nucleophile (pKa < 15)
Mechanism
- Smiles
CC(C)O
- Description
Secondary alcohol
- Smiles
CC(C)O
- Description
PPh₃ + DEAD activate alcohol
- Smiles
CC(C)N3
- Description
Nucleophile displaces with INVERSION
Stereochemistry
Inversion of configuration (like SN2)
Tips
Converts alcohol to other groups with INVERSION
Nucleophiles: azides, phthalimide, carboxylic acids, phenols
pKa of nucleophile must be < 15
Great for stereochemistry manipulation
Related Reactions
sn2-bromide-hydroxide
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