Acetolactone (α-acetolactone) is an organic compound with formula C
2
H
2
O
2
. 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.[2]

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).
☒N verify (what is checkY☒N ?)

Although acetolactone itself has not been isolated in bulk, the related species bis(trifluoromethyl)acetolactone ((CF
3
)
2
C
2
O
2
), which has increased electronic stabilisation due to 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.[3]

See also

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References

edit
  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. ^ 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