Dicyclopentadiene → endo-Dicyclopentadiene

HRID 1516131Notes

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>>[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

Reactant 2

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. One equivalent of phenylacetylene per equivalent of RuClH(H2)(PCy3)2 was added via the addition of 0.1 mls of a 72 mM solution 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, the material was soft and rubbery.

Workup

waitAfter 24 hours

Sources & evidence

ORD record: ord-6311b8284aba44229720bfa27cfb6db8
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08227371B2

Reaction notes

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