Oxidations in Organic Chemistry

R. A. Johnson, Oxidation in Organic Chemistry, Academic Press, Inc., New York, 1978, part C, p. 131. 

In general, peroxomonosulfates have fewer uses in organic chemistry than peroxodisulfates. However, the triple salt is used for oxidizing ketones (qv) to dioxiranes (7) (71,72), which in turn are useful oxidants in organic chemistry. Acetone in water is oxidized by triple salt to dimethyldioxirane, which in turn oxidizes alkenes to epoxides, polycycHc aromatic hydrocarbons to oxides and diones, amines to nitro compounds, sulfides to sulfoxides, phosphines to phosphine oxides, and alkanes to alcohols or carbonyl compounds. 

An expanding development is the use of peroxodisulfates as oxidants in organic chemistry (80,81). These reactions are initiated by heat, light, gamma rays, or transition-metal ions. The primary oxidising species is usually the sulfate ion radical, P hskip -3pt peroxodisulfate anion... 

Obsolete uses of urea peroxohydrate, as a convenient source of aqueous hydrogen peroxide, include the chemical deburring of metals, as a topical disinfectant and mouth wash, and as a hairdresser s bleach. In the 1990s the compound has been studied as a laboratory oxidant in organic chemistry (99,100). It effects epoxidation, the Baeyer-Villiger reaction, oxidation of aromatic amines to nitro compounds, and the conversion of sodium and nitrogen compounds to S—O and N—O compounds. 

A related compound, the peroxohydrate of melamine, C H N, was made by Peroxid-Chemie but discontinued in the 1980s. In addition, a diperoxohydrate of the organic base DABCO is recogni2ed and has been used as an oxidant in organic chemistry, but such a system has been known to explode (101). 

His field of interest is organofluorine chemistry. He has written 68 research papers, 19 review papers, 29 patents, and 15 books (9 in English). His chef-d oeuvres are Chemistry of Organic Fluorine Compounds, Reductions in Organic Chemistry, and Oxidations in Organic Chemistry, published in 1976, 1984, and 1990, respectively. 

For a review of this and related reactions, see Chakrabartty, S.K. in Trahanovsky Oxidation in Organic Chemistry, pt. C Academic Press NY, 1978, p. 343. 

For a review, see Cainelli, G. Cardillo, G. Chromium Oxidations in Organic Chemistry, Springer NY, 1984, p. 8. 

For lists of some of the oxidizing agents used, with references, see Hudlicky, M. Oxidations in Organic Chemistry American Chemical Society Washington, 1990, p. 174 Ref. 92, p. 838 Srivastava, R.G. Venkataramani, P.S. Synth. Commun., 1988, 18, 2193. See also Haines, A.H. Ref. 207. 

Hudlicky M (1990) Oxidations in Organic Chemistry. American Chemical Society, Washington, DC. 

---