Hexachloroethane → endo-Dicyclopentadiene

HRID 1516133Notes

Reaction equation

HRID 1516133 reaction equation
[CH2:1]1[CH:5]2[CH:6]3[CH:10]=[CH:9][CH:8]([CH:4]2[CH:3]=[CH:2]1)[CH2:7]3.ClC(Cl)(Cl)C(Cl)(Cl)Cl.C1(C#C)C=CC=CC=1>C(Cl)Cl>[CH2:1]1[CH:5]2[C@@H:6]3[CH:10]=[CH:9][C@H:8]([CH:4]2[CH:3]=[CH:2]1)[CH2:7]3

Participants

5

Reactant 3

HCID 6214Hexachloroethane2×HCID 6492Dicyclopentadiene2×HCID 10821Phenylacetylene2×

Product 1

HCID 15618652endo-Dicyclopentadiene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 10.0 gram (75.6 mmol) amount of dicyclopentadiene was added to a 100 ml round-bottom flask. A 5.0 milligram (7.2 μmol) amount of RuClH(H2)(PCy3)2, ten equivalents of hexachloroethane, and ten equivalents of phenylacetylene were added via the addition of a 0.5 mls stock solution containing 2.5 mls of CH2Cl2, 25 mg RuClH(H2)(PCy3)2, 86 mg of hexachloroethane and 36 mg of phenylacetylene. The ring opening polymerization of dicyclopentadiene was observed slowly by a gradual thickening of the solution to a rubbery viscous material after three hours. After 24 hours, it had become a soft rubbery material.

Workup

  1. waitAfter 24 hours

Sources & evidence

ORD record
ord-a24c2b503f5543e995f14a249559cdc8
Source dataset
uspto-grants-2012_07
Patent number
US08227371B2

Reaction notes

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