- Jones oxidation
The
Jones oxidation is achemical reaction described as thechromic acid oxidation of primary and secondaryalcohol s tocarboxylic acid s andketone s, respectively. [cite journal | author = Bowden, K.; Heilbron, I. M.; Jones, E. R. H | journal =J. Chem. Soc. | year = 1946 | pages = 39 | doi = 10.1039/jr9460000039 | title = 13. Researches on acetylenic compounds. Part I. The preparation of acetylenic ketones by oxidation of acetylenic carbinols and glycols] [cite journal | author = Heilbron, I.M.; Jones, E.R.H.; Sondheimer, F | journal =J. Chem. Soc. | year = 1949 | pages = 604 | doi = 10.1039/jr9490000604 | title = 129. Researches on acetylenic compounds. Part XV. The oxidation of primary acetylenic carbinols and glycols] [cite journal | author = Bladon, P | journal =J. Chem. Soc. | year = 1951 | pages = 2402 | doi = 10.1039/jr9510002402 | title = 532. Studies in the sterol group. Part LII. Infra-red absorption of nuclear tri- and tetra-substituted ethylenic centres] [cite journal | author = Jones, E. R. H | journal =J. Chem. Soc. | year = 1953 | pages = 457 | doi = 10.1039/jr9530000457 | title = 92. The chemistry of the triterpenes. Part XIII. The further characterisation of polyporenic acid A] [cite journal | author = Jones, E. R. H | journal =J. Chem. Soc. | year = 1953 | pages = 2548 | doi = 10.1039/jr9530002548 | title = 520. The chemistry of the triterpenes and related compounds. Part XVIII. Elucidation of the structure of polyporenic acid C] [cite journal | author = Jones, E. R. H | journal =J. Chem. Soc. | year = 1953 | pages = 3019 | doi = 10.1039/jr9530003019 | title = 599. The chemistry of the triterpenes and related compounds. Part XIX. Further evidence concerning the structure of polyporenic acid A] [cite journal | author =C. Djerassi , R. Engle and A. Bowers | title = Notes - The Direct Conversion of Steroidal 5-3-Alcohols to 5- and 4-3-Ketones | year = 1956 | journal =J. Org. Chem. | volume = 21 | issue = 12 | pages = 1547–1549 | doi = 10.1021/jo01118a627] Jones reagent - a solution ofchromium trioxide in concentratedsulfuric acid - is used as theoxidizing 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, quiteexothermic , 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.
ee also
*
Collins reagent
*Pyridinium chlorochromate
*Sarett oxidation References
Further reading
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