Hexachloroethane → endo-Dicyclopentadiene

HRID 1516128Notes

Reaction equation

HRID 1516128 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.C1(C#C)C=CC=CC=1.ClC(Cl)(Cl)C(Cl)(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

4

Reactant 3

HCID 6214HexachloroethaneHCID 6492Dicyclopentadiene2×HCID 10821Phenylacetylene2×

Product 1

HCID 15618652endo-Dicyclopentadiene

Procedure

A 10.0 gram (75.6 mmol) amount of dicyclopentadiene was added to a 20 ml scintillation vial. A 5.0 milligram (7.2 μmol) amount of RuClH(H2)(PCy3)2 was added. One equivalent of phenylacetylene per equivalent of RuClH(H2)(PCy3)2 was added via the addition of 0.1 mls of 72 mM solution of phenylacetylene. Ten equivalents of hexachloroethane per equivalent of RuClH(H2)(PCy3)2 were charged via the addition of 1.0 mls of a 72 mM solution. The ring opening polymerization of dicyclopentadiene was observed by a gradual thickening of the solution to a rubbery viscous material after six minutes. After one hour, a solid rubbery material had formed.

Workup

  1. waitAfter one hour
  2. customa solid rubbery material had formed

Sources & evidence

ORD record
ord-8ec16d2180e547888a9d1b34974f1558
Source dataset
uspto-grants-2012_07
Patent number
US08227371B2

Reaction notes

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