1,3-Butadienal
Chemical compound
From Wikipedia, the free encyclopedia
1,3-Butadienal, also called vinylketene, is an organic compound and the simplest vinylketene. Like other vinylketenes, it occurs primarily as a reactive intermediate in cycloaddition reactions.
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| Names | |
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| IUPAC name
Buta-1,3-dien-1-one | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| CH2CHCHCO | |
| Molar mass | 68.075 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation
As a vinylketene not protected by steric effects, 1,3-butadienal is typically prepared in situ. Dehydrohalogenation of vinyl acyl chlorides produces vinylketene:[1]
- H2C=CH−CH2−COCl → H2C=CH−CH=C=O + HCl
The molecule was first properly observed in pyrolysis of the ynol ether ethoxybutenyne, a retro-ene reaction:
- H2C=CH−C≡C−O−C2H5 → H2C=CH−CH=C=O + C2H4
An analogous decomposition of ethoxyethyne yields ethenone.[2] The compound also occurs from the radical addition of the allyl and COCl radicals, a potential side reaction in the production of allyl radicals from propene and oxalyl chloride.[3] As a reaction intermediate, it is produced from electrocyclic ring-opening of cyclobutenone.[4]