Azobisisobutyronitrile → Adamantane

HRID 1955963Notes

Reaction equation

HRID 1955963 reaction equation
Br[C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2.CC(N=NC(C#N)(C)C)(C#N)C>C1(C(F)(F)F)C=CC=CC=1>[CH:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2

Participants

4

Reactant 2

HCID 6547AzobisisobutyronitrileHCID 791061-Bromoadamantane

Product 1

HCID 9238Adamantane

Reagents, catalysts & solvents 1

HCID 7368(Trifluoromethyl)benzeneSolvent

Procedure

To a stirred solution of 1-bromoadamantane (100 mg, 0.46 mmol) and tris (2-perfluorohexyl)ethyltin hydride (640 mg, 0.55 mmol) in benzotrifluoride (9.2 mL) was added a catalytic amount of AIBN. The reaction mixture was heated at reflux temperature for 3 h. The solvent was evaporated and the crude residue was partitioned between dichloromethane (20 mL) and perfluoromethylcyclohexane (10 mL). The two layers were separated and the dichloromethane phase was concentrated yielding adamantane as a pure compound (56 mg, 90%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature for 3 h
  3. customThe solvent was evaporated
  4. customthe crude residue was partitioned between dichloromethane (20 mL) and perfluoromethylcyclohexane (10 mL)
  5. customThe two layers were separated
  6. concentrationthe dichloromethane phase was concentrated

Sources & evidence

ORD record
ord-6f63159ee0aa4140a98b2c729bd767ae
Source dataset
uspto-grants-1998_07
Patent number
US05777121

Reaction notes

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