Allyl bromide → Sodium 1-(propan-2-yl)cyclopenta-2,4-dien-1-ide

HRID 981449Notes

Reaction equation

HRID 981449 reaction equation
[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Ni:9].C([Br:13])C=C.[CH:14]([C-:17]1[CH:21]=[CH:20][CH:19]=[CH:18]1)([CH3:16])[CH3:15].[Na+:22]>C1COCC1>[CH:14]([C-:17]1[CH:21]=[CH:20][CH:19]=[CH:18]1)([CH3:16])[CH3:15].[Na+:22].[CH2:15]([Ni:9][Br:13])[CH:14]=[CH2:17]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 2603913463-39-3HCID 16213221Sodium 1-(propan-2-yl)cyclopenta-2,4-dien-1-ide

Product 2

HCID 16213221Sodium 1-(propan-2-yl)cyclopenta-2,4-dien-1-ideHCID 178455859HCID 178455859, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium isopropylcyclopentadienide is prepared in THF as described in Preparation A. Then dimeric allyl nickel bromide is prepared by reacting 70 g of nickel carbonyl and 50 ml of allyl bromide in 200 ml of THF. The final solution is added dropwise onto the solution of sodium isopropylcyclopentadienide and allowed to stir at room temperature for two hours. The mixture becomes violet immediately and NaBr precipitates. The solution containing isopropylcyclopentadienyl nickel allyl is transferred to another flask and solvent is removed by pumping at or below room temperature. The product is removed by vacuum distillation at 10-2 torr in the range of 30°-40° C.

Workup

  1. customas described in Preparation A
  2. customNaBr precipitates
  3. additionThe solution containing isopropylcyclopentadienyl nickel allyl
  4. customis transferred to another flask
  5. customsolvent is removed
  6. custombelow room temperature
  7. customThe product is removed by vacuum distillation at 10-2 torr in the range of 30°-40° C.

Sources & evidence

ORD record
ord-bf8005f5c20f4059b1a58cc43d115631
Source dataset
uspto-grants-1991_02
Patent number
US04992305

Reaction notes

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