Acetolactone

Acetolactone
Structural formula source ↗	Ball-and-stick model source ↗
Names
	IUPAC name Oxiran-2-one
	Preferred IUPAC name Oxiranone
Identifiers
CAS Number	42879-41-4;
3D model (JSmol)	Interactive image;
ChemSpider	393042 Y;
PubChem CID	445391;
CompTox Dashboard (EPA)	DTXSID30332189 ;
	InChI InChI=1S/C2H2O2/c3-2-1-4-2/h1H2 Y Key: HZSIFDFXFAXICF-UHFFFAOYSA-N Y; InChI=1/C2H2O2/c3-2-1-4-2/h1H2 Key: HZSIFDFXFAXICF-UHFFFAOYAQ;
	SMILES O=C1OC1;
Properties
Chemical formula	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). Y verify (what is YN ?) Infobox references

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.

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

References

"Acetolactone". PubChem. National Center for Biotechnology Information.
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
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.
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.
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.

[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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See also

References