Phosphinyl peroxides

Numerous sulfur and phosphorus peroxy compounds such as monopersulfuric acid (Caro s acid, la), monopersulfate (Oxone, Ib), ammonium monopersulfate Ic, tetra n-butyl-ammonium monopersulfate Id, peroxydisulfates 2a and 2b", tetra n-butylammonium peroxydisulfate 2c, symmetrical bissulfonyl peroxide 3 , acyl sulfonyl peroxide 4 , unsymmetrical sulfonyl peroxide 5 , sulfinyl peroxy intermediates 6a, sulfonyl peroxy intermediate 6b, sulfonimidoyl peroxy intermediate 7, bis(diphenyl phosphinyl) peroxide 8 , unsymmetrical phosphorus peroxide 9 and phosphoranyl peroxy intermediate 10" are known. Recently, many researchers have shown interest in the preparation and... 

J, N-DialkyIhydroxylamines were obtained following hydrolyses of IJ-dialkyl-o -diphenylphosphiny 1 hydroxylamines which were in turn prepared by addition of secondary amines to bis[diphenyl-phosphinyl]peroxide at -40°C in alcohol-free chloroform (Scheme... 

Ethyl-2-oxo-4-propyl-XII/2, 36 Peroxid tert.-Butyl-(phosphinyl)-E13/1, 940 (Cl - O-OR) Phosphanoxid Acetoxymethyl-butyl-methyl- E2, 48 (P-Oxigenier.) Phosphonsaure... 

A two-step procedure for the oxidation of amines to hydroxylamines involves nucleophilic displacement along the peroxide bond of dibenzoyl peroxide and saponification of the intermediate O-ben-zoylhydroxylamine. Primary and secondary amines have been oxidized in this way (equation 29). Related reactions for transformation of amines to O-(arylsulfonyl)- and O-phosphinyl-hydroxylamines have been described by means of bis(arylsulfonyl) and bis(diphenylphosphinyl) peroxide, respectively 86,87... 

Treatment of the phosphine analog with acid results in the placement of a phosphorous atom in the pyranose ring. This compound is readily oxidized in air to give the phosphinyl analog which can be further oxidized with hydrogen peroxide to give the phosphinic acid derivative of D-xylopyranose (reaction 4.124). 

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