Acetolactone
In organic chemistry, α‑lactone refers to a functional group, the smallest possible lactone. It is a family of unstable, three-membered heterocycles, containing an epoxide ring fused with a carbonyl group.
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| Names | |||
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| IUPAC name
Oxiran-2-one
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| Preferred IUPAC name
Oxiranone | |||
| Identifiers | |||
3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |||
| C2H2O2 | |||
| Molar mass | 58.036 g·mol−1 | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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The parent, acetolactone (α-acetolactone), is an organic compound with formula C
2H
2O
2, and has not been isolated in bulk. The compound was first described in 1997 as a transient species in mass spectrometry experiments.
Generally, α‑lactones are produced by the cryogenic, photochemical decarboxylation of peroxymalonic anhydrides. Even at 77 K, the products rapidly polymerize or decarbonylate to ketones or aldehydes.
An exception is bis(trifluoromethyl)acetolactone ((CF
3)
2C
2O
2), stabilized by its two trifluoromethyl groups. That compound has a half-life of 8 hours at 25 °C.
Α-Thiolactones can be produced via oxygen transfer from a nitrone to a thioketene.