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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.

Acetolactone
Structural formula
Structural formula
Ball-and-stick model
Ball-and-stick model
Names
IUPAC name
Oxiran-2-one[1]
Preferred IUPAC name
Oxiranone
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C2H2O2/c3-2-1-4-2/h1H2 checkY
    Key: HZSIFDFXFAXICF-UHFFFAOYSA-N checkY
  • InChI=1/C2H2O2/c3-2-1-4-2/h1H2
    Key: HZSIFDFXFAXICF-UHFFFAOYAQ
  • O=C1OC1
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).
checkY verify (what is checkYX markN ?)

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

References

  1. ^ "Acetolactone". PubChem. National Center for Biotechnology Information.
  2. ^ 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. doi:10.1016/S0168-1176(97)00150-X
  3. ^ Chapman, O. L.; Wojtkowski, P. W.; Adam, Waldemar; Rodriguez, O.; Rucktaeschel, R. (1972). "Photochemical transformations. XLIV. Cyclic peroxides. Synthesis and chemistry of .alpha.-lactones". Journal of the American Chemical Society. 94 (4): 1365–1367. Bibcode:1972JAChS..94.1365C. doi:10.1021/ja00759a060.
  4. ^ Adam, Waldemar; Liu, Ju-Chao; Rodriguez, Oswaldo (1973). "Bis(trifluoromethyl)acetolactone, a Stable α-Lactone". The Journal of Organic Chemistry. 38 (12): 2269–2270. doi:10.1021/jo00952a047.
  5. ^ Voss, J. (1979). "The chemistry of thio acid derivatives". In Patai, Saul (ed.). The Chemistry of Acid Derivatives. The Chemistry of Functional Groups, Supplement B. Vol. 1, Part 2. Chichester, WSX: Interscience (Wiley). p. 1038. ISBN 0 471 99611 4. LCCN 75-6913.
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