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[1]
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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).
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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.[2]
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.[3]
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.[4]
Α-Thiolactones can be produced via oxygen transfer from a nitrone to a thioketene.[5]
See also
[edit | edit source]References
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- ^ Detlef Schröder, Norman Goldberg, Waltraud Zummack, Helmut Schwarz, John C. Poutsma and Robert R. Squires (1997), Generation of α-acetolactone and the acetoxyl diradical •CH2COO• in the gas phase. International Journal of Mass Spectrometry and Ion Processes, volumes 165-166, November issue, pages 71-82. Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
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