Hexachloroethane → endo-Dicyclopentadiene

HRID 1516127Notes

Reaction equation

HRID 1516127 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. Five equivalents of phenylacetylene and hexachloroethane per equivalent of RuClH(H2)(PCy3)2 were added via the addition of 0.5 mls of 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, the material was a hard rubbery solid.

Workup

  1. waitAfter 24 hours

Sources & evidence

ORD record
ord-5d01298bb9e345b6b548ff7cbe95c1c2
Source dataset
uspto-grants-2012_07
Patent number
US08227371B2

Reaction notes

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