Hexachloroethane → endo-Dicyclopentadiene

HRID 1516130Notes

Reaction equation

HRID 1516130 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 1.2 milligram (1.7 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. 100 equivalents of hexachloroethane (170 mg) was added. 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, the material was a gel-like.

Workup

  1. waitAfter 24 hours

Sources & evidence

ORD record
ord-d1340e0a30c74600b7bf17a148dacd1e
Source dataset
uspto-grants-2012_07
Patent number
US08227371B2

Reaction notes

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