Jones oxidation

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. [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 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.

ee also

* Collins reagent
* Pyridinium chlorochromate
* Sarett oxidation

References

Further reading

*
*
*


Wikimedia Foundation. 2010.

Игры ⚽ Поможем сделать НИР

Look at other dictionaries:

  • Jones-Oxidation — Die Jones Oxidation ist eine chemische Reaktion der Organischen Chemie, die der Oxidation von Alkoholen und Aldehyden dient. Primäre Alkohole werden hierbei zunächst zu Aldehyden, dann zu Carbonsäuren oxidiert, sekundäre Alkohole zu Ketonen. Als… …   Deutsch Wikipedia

  • Jones-Oxidation — Jones O|xi|da|ti|on [ dʒəʊnz ; nach dem brit. Chemiker E. R. H. Jones (*1911)]: schonende Oxidation von Alkoholen durch schwefelsaure Chromsäurelsg. (Jones Reagenz), die man der Lsg. des Alkohols in Aceton zutropfen lässt …   Universal-Lexikon

  • Oxidation of primary alcohols to carboxylic acids — The oxidation of primary alcohols to carboxylic acids is an important oxidation reaction in organic chemistry. When a primary alcohol is converted to a carboxylic acid, the terminal carbon atom increases its oxidation state by four. Oxidants able …   Wikipedia

  • Oxidation durch hypervalente Iod-Reagenzien — Die Oxidation durch hypervalente Iod Reagenzien umfasst in der organische Chemie die Oxidation von primären bzw. sekundären Alkoholen durch die Oxidationsmittel IBX (2 Iodoxybenzoesäure) und Dess Martin Periodinan. Vor allem die Dess Martin… …   Deutsch Wikipedia

  • Oppenauer oxidation — Oppenauer oxidation, named after Rupert Viktor Oppenauer,[1] is a gentle method for selectively oxidizing secondary alcohols to ketones. The reaction is the opposite of Meerwein Ponndorf Verley reduction. The alcohol is oxidized with aluminium… …   Wikipedia

  • Alcohol oxidation — Mechanism of oxidation of primary alcohols to carboxylic acids via aldehydes and aldehyde hydrates Alcohol oxidation is an important organic reaction. Primary alcohols (R CH2 OH) can be oxidized either to aldehydes (R CHO) or to carboxylic acids… …   Wikipedia

  • Dess-Martin-Oxidation — Die Dess Martin Oxidation ist eine chemische Reaktion, die zur Oxidation von primären und sekundären Alkoholen zu Aldehyden bzw. Ketonen benutzt wird. Als Oxidationsmittel wird das Dess Martin Periodinan verwendet. Es handelt sich um eine sehr… …   Deutsch Wikipedia

  • Sarett oxidation — The Sarett oxidation is the oxidation of an alcohol to a ketone or an aldehyde using chromic oxide and pyridine. Primary alcohols will only be oxidised to the aldehyde and not on to carboxylic acids.:The reagent is named after the American… …   Wikipedia

  • Kornblum-Oxidation — Als Kornblum Oxidation bezeichnet man in der Chemie die Überführung von Alkylhalogeniden (Alkylbromide, Alkyliodide) in die jeweiligen Aldehyde durch einfaches Erhitzen in Dimethylsulfoxid (DMSO) unter Zugabe einer Base wie… …   Deutsch Wikipedia

  • Kornblum oxidation — The Kornblum oxidation is a chemical reaction of a primary halide with dimethyl sulfoxide (DMSO) to form an aldehyde. Like all DMSO based oxidations, the Kornblum oxidation creates an alkoxysulphonium ion, which, in the presence of a base, such… …   Wikipedia

Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”