Hexachloroethane → endo-Dicyclopentadiene

HRID 1516129Notes

Reaction equation

HRID 1516129 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 6214Hexachloroethane2×HCID 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. Ten equivalents of phenylacetylene and hexachloroethane per equivalent of RuClH(H2)(PCy3)2 were added via the addition of 1.0 mls each of a 72 mM solution of phenylacetylene and hexachloroethane, respectively. The ring opening polymerization of dicyclopentadiene was observed by a rapid thickening of the solution to a rubbery viscous material. After 4 minutes, the material was a rubbery solid. After 24 hours, a hard rubbery solid was obtained.

Workup

  1. waitAfter 24 hours
  2. customa hard rubbery solid was obtained

Sources & evidence

ORD record
ord-007d6158701943ed93761023f212f1ac
Source dataset
uspto-grants-2012_07
Patent number
US08227371B2

Reaction notes

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