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.
| Verifiedrevid | 399367733 |
|---|---|
| Pin | Oxiranone |
| Iupacname | Oxiran-2-one[1] |
The parent, acetolactone (α-acetolactone), is an organic compound with formula C2H2O2, and has not been isolated in bulk. The compound was first described in 1997 as a transient species in mass spectrometry experiments.[2]
Generally, αlactones 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 ((CF3)2C2O2), 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
- ^
- ^ 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". The Chemistry of Acid Derivatives. Vol. 1, Part 2. The Chemistry of Functional Groups, Supplement B. Patai, Saul (ed.). Chichester, WSX: Interscience (Wiley). p. 1038. ISBN 0 471 99611 4. LCCN 75-6913.