Hydrochloric Acid → (Fluorenyl)(cyclopentadienyl)(methyl)methane
Reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.CN(C)[CH:16]=[C:17]1[CH:21]=[CH:20][CH:19]=[CH:18]1.[CH3:23][Li].Cl>C1COCC1>[C:1]1([CH:16]([CH:17]2[CH:21]=[CH:20][CH:19]=[CH:18]2)[CH3:23])[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1Participants
Procedure
The cyclopentadienyl-type ligand, (fluorenyl)(cyclopentadienyl)(methyl)methane was prepared as follows. A solution of 5.0 g fluorene (0.030 mole) was treated with 0.030 mole n-butylithium in 200 mL THF and stirred for two hours at room temperature. Then 0.030 mole 6-(dimethyl)aminofulvene was added and the mixture was stirred for five hours. The deep red solution was then reacted with 0.060 mole methyllithium and the mixture was refluxed for 8 to 10 hours to form a dianion. The reaction product was hydrolysed very slowly with cooling. The reaction vessel was cooled in a dry ice bath and the reaction mixture was hydrolysed by very slow dropping of a solution of aqueous HCl in THF. The thus produced CHMe-bridged ligand was extracted with pentane, dried over sodium sulfate, and the solvent was evaporated.
Workup
- stirringthe mixture was stirred for five hours
- temperaturethe mixture was refluxed for 8 to 10 hours
- customto form a dianion
- temperaturewith cooling
- temperatureThe reaction vessel was cooled in a dry ice bath
- extractionThe thus produced CHMe-bridged ligand was extracted with pentane
- dry with materialdried over sodium sulfate
- customthe solvent was evaporated
Sources & evidence
- ORD record
- ord-72310deaa02846f88e0dd2a7666be7cf
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05420320
Reaction notes
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