Ethylene → 5,6-Dihydrodicyclopentadiene Norbornene Ethylene

HRID 1028327Notes

Reaction equation

HRID 1028327 reaction equation
[CH2:1]1[CH:5]2[CH:6]3[CH2:10][CH:9]=[CH:8][CH:7]3[CH:3]([CH2:4]2)[CH2:2]1.[CH:11]12[CH2:17][CH:14]([CH2:15][CH2:16]1)[CH:13]=[CH:12]2.[CH2:18]([Al](CC(C)C)CC(C)C)[CH:19](C)C.C=C>CO.C1(C)C=CC=CC=1>[CH2:2]1[CH:3]2[CH:7]3[CH2:8][CH:9]=[CH:10][CH:6]3[CH:5]([CH2:4]2)[CH2:1]1.[CH:11]12[CH2:17][CH:14]([CH2:15][CH2:16]1)[CH:13]=[CH:12]2.[CH2:18]=[CH2:19]

Participants

7

Reactant 4

HCID 6325Ethylene2×HCID 103522-NorborneneHCID 95605DihydrodicyclopentadieneHCID 16682931Triisobutylaluminum

Product 1

HCID 1317314245,6-Dihydrodicyclopentadiene Norbornene EthyleneYield 877.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
70 °C

Procedure

5,6-dihydrodicyclopentadiene (2.7 g, 20 mmol), norbornene (1.9 g, 20 mmol) and magnetic bars were added into a polymerization reactor in a nitrogen atmosphere, after which toluene was added thereto so as to obtain a total amount of 28 ml. This polymerization reactor was heated to 70° C. with stirring. A catalyst (0.7 mg, 2 μmol) represented by Formula 6, [Ph3C]+[B(C6F5)4]− (7.4 mg, 8 μmol), and triisobutylaluminum (160 mg, 800 μmol) were mixed with 2.0 in of toluene in a dry box, after which the resulting mixture was added into the reactor using a syringe while being stirred at 70° C., and also ethylene gas was fed thereto at a pressure of 40 psig. After 7 min, the ethylene pressure was released, and the reactor was opened, and 30 ml of methanol was added and thus the reaction product precipitated. Filtration was performed, thus obtaining a powder. The powder was decompressed to a vacuum at 100° C., so that the remaining solvent was removed from the precipitate, thereby obtaining 1.8 g of a polymer material.

Workup

  1. customso as to obtain a total amount of 28 ml
  2. additionafter which the resulting mixture was added into the reactor
  3. stirringwhile being stirred at 70° C.
  4. customthus the reaction product precipitated
  5. filtrationFiltration
  6. customthus obtaining a powder
  7. customwas decompressed to a vacuum at 100° C., so that the remaining solvent
  8. customwas removed from the precipitate

Sources & evidence

ORD record
ord-ff8cc1f5783b42aeb033f0a5a6af6f24
Source dataset
uspto-grants-2014_05
Patent number
US08735521B2

Reaction notes

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