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Jones oxidation



The Jones oxidation is a chemical reaction described as the chromic acid oxidation of primary and secondary alcohols to carboxylic acids and ketones, respectively.[1][2][3][4][5] Jones reagent - a solution of chromium trioxide in concentrated sulfuric acid - is used as the oxidizing agent.

The solvent acetone markedly affects the properties of the chromic acid. The oxidation is very rapid, quite exothermic, and the yields are typically high. The reagent rarely oxidizes unsaturated bonds.

Unfortunately, the chromium residue is very toxic, and care must be taken to dispose of it properly.

References

  1. ^ Bowden, K.; Heilbron, I. M.; Jones, E. R. H. J. Chem. Soc. 1946, 39.
  2. ^ Heilbron, I.M.; Jones, E.R.H.; Sondheimer, F. J. Chem. Soc. 1949, 604.
  3. ^ Bladon, P. et al. J. Chem. Soc. 1951, 2402.
  4. ^ Jones, E. R. H. et al. J. Chem. Soc. 1953, 457 & 2548 & 3019.
  5. ^ C. Djerassi, R. Engle and A. Bowers (1956). "Notes - The Direct Conversion of Steroidal Δ5-3β-Alcohols to Δ5- and Δ4-3-Ketones". J. Org. Chem. 21 (12): 1547-1549. doi:10.1021/jo01118a627.
  • Ley, S. V.; Madin, A. Comp. Org. Syn. 1991, 7, 253-256. (Review)
  • E. J. Eisenbraun (1973). "Cyclooctanone". Org. Synth.; Coll. Vol. 5: 310. 
  • J. Meinwald, J. Crandall, and W. E. Hymans (1973). "Nortricyclanone". Org. Synth.; Coll. Vol. 5: 866. 

See also
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Jones_oxidation". A list of authors is available in Wikipedia.
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