Methanol → 3,7-Biscyclopentadienylidenebicyclo[3,3,0]octane

HRID 1756235Notes

Reaction equation

HRID 1756235 reaction equation
[CH:1]12[CH2:8][C:7](=O)[CH2:6][CH:5]1[CH2:4][C:3](=O)[CH2:2]2.[CH:11]1[CH2:15][CH:14]=[CH:13][CH:12]=1.N1[CH2:20][CH2:19][CH2:18][CH2:17]1.[CH3:21]O>>[C:12]1(=[C:3]2[CH2:4][CH:5]3[CH:1]([CH2:8][C:7](=[C:17]4[CH:21]=[CH:20][CH:19]=[CH:18]4)[CH2:6]3)[CH2:2]2)[CH:11]=[CH:15][CH:14]=[CH:13]1

Participants

5

Reactant 4

HCID 887MethanolHCID 7612CyclopentadieneHCID 31268PyrrolidineHCID 103526cis-Tetrahydropentalene-2,5(1H,3H)-dione

Product 1

HCID 151747353,7-Biscyclopentadienylidenebicyclo[3,3,0]octane

Procedure

In a 300-cm3 four-necked flask in which the atmosphere was replaced with nitrogen, 4.9 g of bicyclo[3,3,0]octane-3,7-dione and 12 g of cyclopentadiene were dissolved in 100 cm3 of methanol. 12 cm3 of pyrrolidine was added dropwise to the solution at 0° C. over 30 minutes, and the produced solid was collected by filtration, washed with methanol, and then dried to obtain 5.3 g of yellow 3,7-biscyclopentadienylidenebicyclo[3,3,0]octane. [3,7-dicyclopentadienyl-3,7-difluorenylbicyclo[3,3,0]octane]

Workup

  1. filtrationthe produced solid was collected by filtration
  2. washwashed with methanol
  3. customdried

Sources & evidence

ORD record
ord-c381d3fce20543eba1a6fbf82f57cd14
Source dataset
uspto-grants-1995_08
Patent number
US05439994

Reaction notes

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