Potassium permanganate with periodate

Many classical oxidations are frequently performed in aqueous media, using oxidants such as potassium permanganate, sodium periodate, or sodium or calcium hypochlorite (Hudlicky, 1990). Cyclohexene can now be oxidized directly to colorless crystalline adipic acid with aqueous 30 percent hydrogen peroxide under organic solvent-and halide-free conditions, as discussed earlier (Sato et al., 1998) (see fig. 6.1). 

Delay compositions are mixtures of materials which, when pressed into delay tubes, react without evolution of gaseous products and thus ensure the minimum variation in the delay period. Examples of such mixtures are potassium permanganate with antimony lead dioxide or minium with silicium redox reactions with fluorides and other halides (- also Coruscatives and -+ delay gasless). 

Solasodenone (24) has been oxidized with potassium permanganate-sodium periodate to yield the keto-acid (25). The same starting material gave (26) on Wollf-Kishner reduction of the ketone moiety followed by treatment of the product with lithium aluminium hydride the corresponding 4,5a- and 4,5/3-dihydro-derivatives of (26) were similarly prepared. ... 

The same products are formed when citric acid is oxidized by acidic solutions containing mixtures of potassium permanganate with KIO3, Kt or but also yellow solid is precipitated, probably tetraiodoacetone ( 2)2(20 [269], The oxidation reactions of citric acid by periodic acid were also discussed by Melangeau and Rub-man [270]. The over-all oxidation process includes an additional product oxalic acid... 

The use of potassium permanganate (KMn04) is applied to filters clogged with algae. A eoncentrated solution containing potassium permanganate is spread at an effective eoncentration over the surfaee of the filters to obtain, a eharaeteristie pink-purple eolor on the top of the mass and allowed to infiltrate the bed for a 24 hour period. After this operation, the filter is earefully washed once again. 

Preparation of Intermediate Compound 4-Chloro-5-Sulfamyl-N-Acetylanthranilic Acid To a hot solution (80°C) of 366 g (1.482 mols) of magnesium sulfate (Epsom salts) in 2.8 liters of water was added 130 g (0.495 mol) of powdered 5-chloro-2-methyl-4-sulfamyl-acetanilide. With stirring and maintaining the temperature at 83°C, 234 g (1.482 mols) of potassium permanganate was added portionwise over a period of 2 hours. The mixture was then kept at 85°C with stirring for an additional 3 hours. By this time the pink color of the permanganate had been discharged. 

The oxidation of diethyl 3,6-hexanooxepin-4,5-dicarboxylate with a mixture of sodium periodate and potassium permanganate as oxidizing agent gives diethyl 3-[(formyioxy)methylene]-l 0-oxocyclodec-l-en-l,2-dicarboxylate (2) in 91 % yield.130 A minor modification of the reaction conditions gives two products 2 (35 %) and a product which retains the oxepin structure (23 %) identified as the same lactone described in Section 1.2.1.1.129... 

When the hexamethylene bridge already contains a ketone function, the corresponding cyclo-decenedione derivative 3 is obtained upon regioselective oxidation of the C-C double bond a with potassium permanganate and sodium periodate.38... 

A solution of 25.8 g. (0.20 mole) of 4-amino-2,2,4-trimethyl-pentane (ierf-octylamine) (Note 1) in 500 ml. of C.P. acetone is placed in a 1-1. three-necked flask equipped with a Tru-Bore stirrer and a thermometer and is diluted with a solution of 30 g. of magnesium sulfate (Note 2) in 125 ml. of water. Potassium permanganate (190 g., 1.20 moles) is added to the well-stirred reaction mixture in small portions over a period of about 30 minutes (Note 3). During the addition the temperature of the mixture is maintained at 25-30° (Note 4), and the mixture is stirred for an additional 48 hours at this same temperature (Note 5). The reaction mixture is stirred under water-aspirator vacuum at an internal temperature of about 30° until most of the acetone is removed (Note 6). The resulting viscous mixture is steam-distilled approximately 500 ml. of water and a pale-blue organic layer are collected. The distillate is extracted with pentane, the extract is dried over anhydrous sodium sulfate, and the pentane is removed by distillation at atmospheric pressure. The residue is distilled through a column (Note 7) at reduced pressure to give 22-26 g. (69-82%) of colorless 4-nitro-2,2,4-trimethylpentane, b.p. 53-5473 mm., < 1.4314, m.p. 23.5-23.7°. 

Ny lon-6 (108 g) carpet backed with calcium-carbonate-filled latex and polypropylene was charged to a 1000-mL three-neck round-bottom flask (equipped with a condenser) with 6 mL of 85% phosphoric acid. Superheated steam was injected continuously during a 45-min period. The vapor temperature of the reaction medium was 250-300°C. The volume of distillate collected was 1065 mL. The distillate contained 1.9% e-caprolactam (as determined by GC), which corresponded to a crude yield of 37.5%. The distillate was fractionated in a distillation column and the nonaqueous phase removed. The remaining aqueous phase was treated with 2% potassium permanganate at 40-50°C for 2 h. Evaporation of... 

A. 2-Methyl-2-nitropro]f)ane. To a well-stirred suspension of 650 g. (4.11 moles) of potassium permanganate in 3 1. of water, contained in a 5-1. three-necked flask fitted with a reflux condenser, a mechanical stirrer, a thermometer, and a 250-ml. dropping funnel, is added dropwise and with stirring over a 10-minute period, 100 g. (1.37 moles) of i-butylamine (Note 1). When the addition is complete, the reaction mixture is heated to 55° over a period of approximately 2 hours, and then the reaction mixture is maintained at 55° with continuous stirring for 3 hours. The dropping funnel and reflux condenser are replaced by a stopper and a still head fitted for steam distillation and the product is steam distilled from the reaction mixture (Note 2). The liquid product is separated from the denser water layer and then diluted with 250 ml. of ether and washed successively with two 50-ml. portions of aqueous 2M hydrochloric acid and with 50 ml. of water. After the ethereal solution has been dried over anhydrous magnesium sulfate, the solution is fractionally distilled at atmospheric pressure to remove the ether. The residual crude product (Note 3) amounts to 106-128 g. and is sufficiently pure for use in the next step. In a typical run, distillation of 124 g. of the crude product afforded 110 g. (78%) of the pure 2-methyl-2-nitrobutane as a colorless liquid, b.p. 127-128°, d 1.3992. The material slowly solidifies on standing to a waxy solid, m.p. 25-26° (Note 4). 

Photolysis of J gives an isomeric compound K in 83% yield. Alkaline hydrolysis of K affords a hydroxy carboxylic acid L, C25H32O4. Treatment of K with silica gel in hexane yields M, C24H2g02. M is converted by sodium periodate-potassium permanganate to a mixture of N and O. What are the structures of K, L, and M ... 

Potassium periodate can be prepared by oxidation of potassium iodate with a powerful oxidizing agent such as potassium permanganate, chlorine or bromine in basic solution ... 

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