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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1160024Generated: October 25, 2026

Toluene → 5-Norbornene 2-allylacetate 5-butylnorbornene 5-norbornene-2-carboxylic methylester

https://huagongshe.com/reaction/1160024

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantBicyclo[2.2.1]hept-2-ene, 5-butyl-HCID 168020—
ReactantMethyl bicyclo[2.2.1]hept-5-ene-2-carboxylateHCID 250075—
Reactant5-Norbornene 2-allylacetateHCID 86597587—
Catalystpalladium(II) acetateHCID 167845—
SolventEthanolHCID 702—
SolventDichloromethaneHCID 6344—
Product5-Norbornene 2-allylacetate 5-butylnorbornene 5-norbornene-2-carboxylic methylesterHCID 86603901—

Reaction Conditions

Temperature90 °C

Reaction Steps

5-norbornene-2-allylacetate (5 mL, 30.9 mmol), 5-butylnorbornene (1.2 mL, 6.6 mmol), 5-norbornene-2-carboxylic methylester (1 mL, 6.6 mmol) and toluene (12.4 mL) were charged into a 250 mL Schlenk flask. Pd(OAc)2 (0.66 mg, 2.94 μmol) and [(Cy)3PH][(B(C6F5)4) (5.65 mg, 5.88 μmol) were dissolved in CH2Cl2 (1 mL) and added to the monomer solution. While the reaction mixture was stirred for 18 hours at 90° C., the reaction mixture became viscous. After the reaction was completed, 120 ml of toluene was added to the viscous solution to dilute it. The solution was poured into an excess of ethanol to precipitate a white polymer, which was filtered through a glass funnel, washed with ethanol, and dried in vacuo at 80° C. for 24 hours to yield 5-norbornene-2-allylacetate/5-butylnorbornene/5-norbornene-2-carboxylic methylester polymer (6.45 g: 90.5% by weight based on the total weight of used monomers). The weight average molecular weight (Mw) of the polymer was 211,891 and Mw/Mn was 2.67.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07814713B2
Source datasetuspto-grants-2010_10
ORD IDord-73911c09baf34fb89d312d7a9b4426db
Source noteuspto-grants-2010_10