Jones oxidation

What is Jones oxidation?

Jones oxidation is a chemical reaction used in organic synthesis to oxidize primary and secondary alcohols to the corresponding aldehydes and ketones, respectively. It is named after its developer, William Jones, who first reported the reaction in the late 19th century..

Jones oxidation
Jones oxidation

In the Jones oxidation reaction, the alcohol is reacted with a chemical oxidizing agent, typically chromium trioxide CrO3 dissolved in aqueous sulfuric acid. The reaction proceeds through a series of steps, including the formation of an intermediate compound called a chromate ester. The chromate ester is then hydrolyzed to the final product, an aldehyde or ketone..

One of the key advantages of the Jones oxidation is its high yield and good selectivity. It is also a relatively simple reaction that can be carried out under mild conditions. However, it does require the use of a strong and potentially hazardous oxidizing agent, which must be handled with care..

Jones oxidation has a wide range of applications in the synthesis of a variety of organic compounds, including pharmaceuticals, fragrances, and flavorings. It has also been used in the synthesis of polymers and materials for electronic applications..

Summary

Jones oxidation is a valuable tool for the synthesis of aldehydes and ketones and has had a significant impact on the field of organic synthesis. It continues to be widely used in the synthesis of a variety of organic compounds..

References

  • K. Bowden et al., J. Chem. Soc. 1946, 39
  • P. Bladon et al., J. Chem. Soc. 1951, 2402
  • E.R.AH. Jones et al., J. Chem. Soc. 1953, 457
  • E.R.AH. Jones et al., J. Chem. Soc. 1953, 2548
  • E.R.AH. Jones et al., J. Chem. Soc. 1953, 3019
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