Jones oxidation

From Wikipedia, the free encyclopedia

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][6][7]} Jones reagent - a solution of chromium trioxide in concentrated sulfuric acid - is used as the oxidizing agent.

The Jones Reagent will also completely oxidize aldehydes to carboxylic acids.

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.

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

[edit] See also

• Collins reagent
• Pyridinium chlorochromate
• Sarett oxidation

[edit] References

1. ^ Bowden, K.; Heilbron, I. M.; Jones, E. R. H (1946). "13. Researches on acetylenic compounds. Part I. The preparation of acetylenic ketones by oxidation of acetylenic carbinols and glycols". J. Chem. Soc.: 39. doi:10.1039/jr9460000039. 
2. ^ Heilbron, I.M.; Jones, E.R.H.; Sondheimer, F (1949). "129. Researches on acetylenic compounds. Part XV. The oxidation of primary acetylenic carbinols and glycols". J. Chem. Soc.: 604. doi:10.1039/jr9490000604. 
3. ^ Bladon, P (1951). "532. Studies in the sterol group. Part LII. Infra-red absorption of nuclear tri- and tetra-substituted ethylenic centres". J. Chem. Soc.: 2402. doi:10.1039/jr9510002402. 
4. ^ Jones, E. R. H (1953). "92. The chemistry of the triterpenes. Part XIII. The further characterisation of polyporenic acid A". J. Chem. Soc.: 457. doi:10.1039/jr9530000457. 
5. ^ Jones, E. R. H (1953). "520. The chemistry of the triterpenes and related compounds. Part XVIII. Elucidation of the structure of polyporenic acid C". J. Chem. Soc.: 2548. doi:10.1039/jr9530002548. 
6. ^ Jones, E. R. H (1953). "599. The chemistry of the triterpenes and related compounds. Part XIX. Further evidence concerning the structure of polyporenic acid A". J. Chem. Soc.: 3019. doi:10.1039/jr9530003019. 
7. ^ 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. 

[edit] Further reading

• Ley, S. V.; Madin, A. (1991). (Review)Comp. Org. Syn. 7: 253–256. 
• E. J. Eisenbraun (1973), "Cyclooctanone", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv5p0310 ; Coll. Vol. 5: 310 
• J. Meinwald, J. Crandall, and W. E. Hymans (1973), "Nortricyclanone", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv5p0866 ; Coll. Vol. 5: 866