Acetolactone

Acetolactone or α-acetolactone is an organic compound with formula C2H2O2. It is the smallest member of the lactone family but can also be described as the epoxide of ethenone. The compound was described in 1997 as a transient species in mass spectrometry experiments.[1]

Acetolactone
Structural formula
Structural formula
Ball-and-stick model
Ball-and-stick model
Names
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=C1CO1
  • 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).
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Infobox references

Although acetolactone itself has not been isolated in bulk, the related species bis(trifluoromethyl)acetolactone ((CF3)2C2O2), which enjoys a degree of electronic stabilisation from its two trifluoromethyl groups, is known and has a half-life of 8 hours at 25 °C. This compound is prepared by photolysis of bis(trifluoromethyl)malonyl peroxide.[2]

See also

References
  1. 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
  2. Waldemar Adam, Ju-Chao Liu, Oswaldo Rodriguez (1973), Bis(trifluoromethyl)acetolactone, a Stable α-Lactone. J. Org. Chem., volume 38, pages 2269–2270 doi:10.1021/jo00952a047


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