Carbon Dioxide → 3-Ethylidene-5-(prop-1-en-1-yl)oxolan-2-one

HRID 1074614Notes

Reaction equation

HRID 1074614 reaction equation
[CH2:1]=[CH:2][CH:3]=[CH2:4].[C:5](=[O:7])=[O:6]>P.[Pd]>[CH:2](=[C:3]1[CH2:4][CH:1]([CH:2]=[CH:3][CH3:4])[O:7][C:5]1=[O:6])[CH3:1]

Participants

4

Reactant 2

HCID 280Carbon DioxideHCID 78451,3-Butadiene

Product 1

HCID 538939023-Ethylidene-5-(prop-1-en-1-yl)oxolan-2-oneYield 0.4%

Reagents, catalysts & solvents 1

HCID 2241076578452-78-5Catalyst

Procedure

Inoue et al., Chem Comm. 1976, 65 describes a process in which butadiene is reacted with carbon dioxide in a polar aprotic solvent in the presence of certain palladium-phosphine complexes (e.g. Pd (Ph2PCH2CH2PPh2)2) to give a five membered lactone, 2-ethylidene-hept-5-en-4-olide, in small yields (0.4 to 12.3% yield based on butadiene), together with much higher yields of butadiene oligomers (60-85% yield).

Sources & evidence

ORD record
ord-4637e64d7cce48cdb57534ff0c10b653
Source dataset
uspto-grants-1983_07
Patent number
US04393224

Reaction notes

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