Acetolactone

Acetolactone
IUPAC name

oxiran-2-one
Identifiers
CAS number 42879-41-4
ChemSpider 393042 Y
Jmol-3D images Image 1
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Properties
Molecular formula C2H2O2
Molar mass 58.04 g mol−1
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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

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