Oxidation with sodium chlorite

One feature of this oxidation system is that it can selectively oxidize primary alcohols in preference to secondary alcohols, as illustrated by Entry 2 in Scheme 12.5. The reagent can also be used to oxidize primary alcohols to carboxylic acids by a subsequent oxidation with sodium chlorite.34 Entry 3 shows the selective oxidation of a primary alcohol in a carbohydrate to a carboxylic acid without affecting the secondary alcohol group. Entry 5 is a large-scale preparation that uses NaC102 in conjunction with bleach as the stoichiometric oxidant. 

Following the periodate oxidation, the 2,3-dialdehyde celluloses were either reduced with potassium borohydride to form the dialcohol or oxidized with sodium chlorite to give dicarboxyl celluloses. The strength loss of the former products was kept lower than 27% and that of the latter 37%. 

As the oxidation of the alcohols with chromium trioxide, or pyridinium dichromate in DMF gave unsatisfactory yields of the target dienoic acids, we tried Swern-oxidation to the aldehyde followed by further oxidation with sodium chlorite. This sequence proved to be highly successful as the Swern-oxidation provided an 80% yield. Subsequent oxidation of the aldehyde using sodium chlorite and 2,3-dimethyl-butene as the scavenger was almost quantitative to produce highly pure tmns-, cis-13-octadecadienoic acid (29). 

Glucose in a mixture with fructose can be determined quantitatively by oxidation with sodium chlorite at pH 4.0 the chlorine dioxide evolved in the reaction is measured 211a). 

Electrochemical Generation of Chlorine Dioxide from Chlorite. The electrochemical oxidation of sodium chlorite is an old, but not weU-known method of generating chlorine dioxide. Concentrated aqueous sodium chlorite, with or without added conductive salts, is oxidized at the anode of an electrolytic cell having a porous diaphragm-type separator between the anode and cathode compartments (122—127). The anodic reaction is... 

Hypophosphoric acid, (H0)2P(0)-P(0)(0H)2, is usually prepared by the controlled oxidation of red P with sodium chlorite solution at room temperature the tetrasodium salt, Na4P2O6.10H2O, crystallizes at pH 10 and the disodium salt at pH 5.2 ... 

Chlorine oxidation of sodium chlorite has also been used on both an industrial scale (by mixing concentrated aqueous solutions) or on a laboratory scale (by passing CVair through a column packed with the solid chlorite) ... 

OXIDATION OF PRIMARY ALCOHOLS TO CARBOXYLIC ACIDS WITH SODIUM CHLORITE CATALYZED BY TEMPO AND BLEACH 4-METHOXYPHENYLACETIC ACID... 

Primary and secondary aliphatic nitro compounds have been oxidized to aldehydes and ketones, respectively (RR CHN02 RR C=0) with sodium chlorite under phase-transfer conditions, TPAP, Oxone , as well as with other reagents. 

Mono-, di-, and trisubstituted olefins undergo osmium-catalyzed enantioselective dihydroxylation in the presence of the (R)-proline-substituted hydroquinidine 3.9 to give diols in 67-95% yields and in 78-99% ee.75 Using potassium osmate(VI) as the catalyst and potassium carbonate as the base in a tm-butanol/water mixture as the solvent, olefins are dihydroxylated stereo- and enantioselectively in the presence of 3.9 and potassium ferricyanide with sodium chlorite as the stoichiometric oxidant the yields and enantiomeric excesses of the... 

As an alternative to oxidative bleaching with sodium chlorite, acrylic fibres may be given a reductive bleach using sodium bisulphite in the presence of oxalic acid. This method is... 

Oxidation of the tetrahydroindolizine 338 with sodium chlorite gives the lactam 339, which rapidly lactonizes to give the pyranoindolizine 340 (Equation 122) <2001T8647>, and the one-pot , three-component reaction between the keto ester 235, acrolein, and o-aminophenol (formally analogous to that of Equation 63) gives the benzoxazolo-naphthyridine 341 (Equation 123) <20010L2145>. 

This methodology provides a general synthesis of L-amino acids in 92-96% ee and in chemical yields of about 40-60%. Thus reaction of 3 (X = Br) with NaN3 under phase-transfer conditions provides 6, which is homologated to the 1-chloro-2-azidoboronate 7. This product is oxidized by sodium chlorite directly to an azido carboxylic acid (8). Hydrogenation of 8 provides L-amino acids (9). 

Benzo[ ]perimidinone carbaldehyde and carboxylic acid derivatives have also been prepared by alkyl oxidation. Thus, treatment of the 2-methyl derivative 588 with selenium dioxide at reflux in dioxane gave the aldehyde 589, which then gave carboxylic acid 590 on reaction with sodium chlorite <2001JME2004>. 

Carbonyl group contents of Al-cellulose increased with prolonging the sodium periodate oxidation time, with very little formation of carboxyl groups. Oxidizing Al-cellulose with sodium chlorite converted 90-97% of carbonyl groups into carboxyl groups (Cd-cellulose). The results indicate that the bond between C2 and C3 position of glucose unit is open. 

Of the various methods for preparing disodium dihydrogen hypophosphate, the one depending upon the oxidation of red phosphorus with sodium chlorite seems to be the best, considering both the yield and the simplicity of the procedure. In this reaction, phosphites and orthophosphates... 

The reactivity of an oxidizer varies depending on the combustible substance used. Sulfur and red phosphorus are higher in reactivity with sodium chlorite and sodium chlorate than ethylene glycol. 

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