Peroxypropionic acid

There are two broad classes of organic peroxyacids peroxycarboxyUc acids, R[C(0)00H], where R is an alkyl, aralkyl, cycloalkyl, aryl, or heterocycHc group and n = 1 or 2, and organoperoxysulfonic acids, RSO2—OOH. PeroxycarboxyUc acids are commonly named by adding the prefix peroxy to the parent acid as in peroxypropionic acid. The prefix per- is accepted only for the weU-estabHshed products, ie, performic, peracetic, and perbenzoic acids. 

More stable than its lower homologues, it merely deflagrates on heating. Higher homologues appear to be still more stable [1], Safe procedures (on the basis of detonability experiments) for preparation of anhydrous solutions of peroxypropionic acid in chloroform or ethyl propionate have been described [2],... 

Benzeneperoxyseleninic acid, 2330 Benzeneperoxysulfonic acid, 2334 3-Chloroperoxybenzoic acid, 2672 Diperoxyazelaic acid, 3183 Diperoxyterephthalic acid, 2920 Monoperoxysuccinic acid, 1537 Peroxyacetic acid, 0833 Peroxybenzoic acid, 2729 3-Peroxycamphoric acid, 3342 Peroxycrotonic acid, 1530 Peroxyformic acid, 0419 Peroxyfuroic acid, 1831 Peroxyhexanoic acid, 2508 Peroxypropionic acid, 1232 Peroxytrifluoroacetic acid, 0662 Trichloroperoxyacetic acid, 0655 POLYMERIC PEROXYACIDS See I,I-DI(BENZOYLPEROXY)ARYLIODINES See also ORGANIC PEROXIDES... 

In the same year, an optically active oxaziridine with nitrogen as the only chiral center was prepared by the treatment of A -diphenylmethylenemethylamine 15 with (S)-(+)-monopercamphoric acid, (S)-(+)-2-(a-naphthyl)peroxypropionic acid, (R> (—)-2-phenylperoxypropionic acid, and (S)-(+)-2-methyiperoxybutyric acid to give 2-methyl-3,3-diphenyloxaziridine with optical rotations of [a] = — 49.2°, — 8.5°, + 12.5°, and — 5.7°, respectively. ... 

Mercaptals of pentoses and hexoses are converted into sulfonals (di-sulfones), which easily undergo dehydration. The dimethylmercaptal of D-ribose or D-arabinose gives, on oxidation with peroxypropionic acid, 1,1-bis(methylsulfonyl)-D-er> f/iro-pentos-l-ene (equation 571) [340. ... 

Hough, L, Taha, M I, The disulphones derived by oxidation of 2-amino-2-deoxy-D-glucose diethyl dithioacetal hydrochloride and its A-acetyl derivative with peroxypropionic acid, J. Chem. Soc., 3564-3572, 1957. 

The reactivity of 120 is much less than that of either a normal alkene or a dithioacetal. Attempts to hydrogenolyze (see Section IV,3) or reduce 120 with Raney nickel, to hydrolyze the dithioacetal (see Section IV,1) with mercury(II) chloride (even in the presence of an overwhelming excess of the reagent), and to ozonize the double bond at —78°, produce only the starting material an analytical sample was prepared by extended treatment of the crude product with a concentrated, aqueous, alkaline solution of potassium permanganate at the reflux temperature.20 Acetolysis, ozonolysis, or brominolysis of 120 at room temperature affords diphenyl disulfide, and extended oxidation with hydrogen peroxide in acetone, with peroxypropionic acid, and with peroxyacetic acid, produces benzene-sulfonic acid, methyl phenyl sulfone, and an uncharacterized explosive, respectively the products occur as intractable mixtures, and the yields are invariably low. 

The dialdose tetraacetate obtained was identical with that previously-prepared, and was further characterized by oxidation, with peroxypropionic acid, to tetra-O-acetylgalactaric acid. 

It was characterized by oxidation with peroxypropionic acid to the crystalline tetra-O-acetylallaric acid. Saponification of the tetraacetate gave allaric acid, which was converted to several derivatives. The 2,3 4,5-di-0-isopropylidene acetal of alZo-hexodialdose was obtained by lead tetraacetate oxidation of l,2 3,4-di-0-isopropylidene-epf-inositol, as briefly reported by Angyal and C. G. MacDonald. ... 

With the pentoses and 6-deoxyhexoses, from which pyranoid compounds analogous to (149) cannot be formed, both the saturated, and unsaturated, acyclic products have been isolated from reaction mixtures. For example, L-rhamnose, affords, on oxidation with peroxypropionic acid in aqueous dioxane, the crystalline, simple sulfone and unsaturated... 

D-Arabinose 88 l-Deoxy-l,l-bis(ethylsulfonyl)-D-mannitol (1 g) (prepared by oxidation of D-mannose diethyl dithioacetal with peroxypropionic acid in dioxan) is made into a slurry with water (10 ml), and then concentrated aqueous ammonia solution (1 drop) is added. The sulfone dissolves rapidly and after 30 min the precipitated diethyl methylene disulfone is filtered off. The filtrate is extracted four times with chloroform (10-ml portions), and the aqueous phase is evaporated in a vacuum at 40°. The residue is treated with hot methanol (5 ml) and after being kept for 24 h at 4° affords / -D-arabinose (0.32 g, 86%), [a]D20 —102° (c 3.5 at equilibrium in water). 

---