Oxidation of OrganoBorane

• Stereospecific Cis(Syn Addition)

• Regioselctive(Anti-Markovnikov)

• Net Reaction

  • (CH3CH2CH2)3B + H2O2 ---> (CH3CH2CH2-O)3B
  • (CH3CH2CH2-O)3B + OH - -->
  • 3 CH3CH2CH2OH + BO3 -

• Reaction Mechanism

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Net Reaction

(CH3-CH2-CH2)3-B + H2O2/OH- ----> 3CH3-CH2-CH2-OH +

BO3 -

Reaction Mechanism

1. H2O2 + OH- ---> H-O-O - + H2O

2. (CH3-CH2-CH2)3-B + H-O-O - --> (CH3-CH2-CH2)3-B -O-O-H

3. (CH3-CH2-CH2)3-B -O-O-H ----->

(CH3-CH2-CH2)2-B -O- CH2-CH2-CH3 + OH -

4. Repeat Steps 2,3 twice more

5. (CH3-CH2-CH2-O)3-B + 3 OH - ----> 3CH3-CH2-CH2-O-H +

BO3 -