Potassium permanganate-sodium periodate

The position and geometry of the side chain double bonds can be determined by ozonolysis and a potassium permanganate-sodium periodate oxidation, as well as by the IR spectrum. Results have shown that the side chain double bonds are always Z 16,122,126). 

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). 

The oxidative degradation of the resin acids has been studied to make available synthetic intermediates. Potassium permanganate-sodium periodate... 

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 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°. 

Palladium(II) oxide, 4825 Palladium(IV) oxide, 4835 Perchloric acid, 3998 Periodic acid, 4425 Permanganic acid, 4434 Peroxodisulfuric acid, 4482 Peroxodisulfuryl difluoride, 4328 Peroxomonosulfuric acid, 4481 Peroxytrifluoroacetic acid, 0666 Platinum hexafluoride, 4371 Platinum(IV) oxide, 4836 Plutonium hexafluoride, 4372 Potassium bromate, 0255 Potassium chlorate, 4017 Potassium dichromate, 4248 Potassium iodate, 4619 Potassium nitrate, 4650 Potassium nitrite, 4649 Potassium perchlorate, 4018 Potassium periodate, 4620 Potassium permanganate, 4647 Rhenium hexafluoride, 4373 Rubidium fluoroxysulfate, 4309 Ruthenium(VIII) oxide, 4862 Selenium dioxide, 4838 Selenium dioxide, 4838 Silver permanganate, 0021 Sodium chlorate, 4039 Sodium chlorite, 4038 Sodium dichromate, 4250 Sodium iodate, 4624 Sodium nitrate, 4721 Sodium nitrite, 4720... 

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 ... 

Exercise 16-37 An elegant modification of the two-step procedure to prepare ketones from alkenes by hydroxylation and oxidative cleavage of the diol formed uses a small amount of potassium permanganate (or osmium tetroxide, 0s04) as the catalyst and sodium periodate as the oxidizing agent ... 

Prepare a solution of 6 g of potassium permanganate in a mixture of 20 ml of 5 per cent sodium hydroxide solution and 150 ml of water, add 2.0 g of p-cresyl methyl ether and heat under reflux for 2-3 hours. If any permanganate remains at the end of this period, destroy it by the addition of a few drops of ethanol. Remove the precipitated manganese dioxide by filtration at the pump, evaporate the filtrate to a volume of 25-30 ml and acidify it (to Congo red) with dilute sulphuric acid. Anisic acid, m.p. 183-184°C, crystallises out on cooling. 

Small Quantities. Work in the fume hood. Wear eye protection, nitrile rubber gloves and laboratory coat. Place 6.0 g (7 mL, 0.107 mol) of acrolein in a 1 L, three-necked, round-bottom flask equipped with a thermometer, stirrer, and dropping funnel. Over a period of 10 minutes, add 50 mL of a solution of 63 g (0.4 mol) of potassium permanganate in 700 mL of water. If the purple color is not discharged, warm the mixture on steam bath until it becomes brown. Add the remainder of the permanganate solution at such a rate that the temperature does not exceed 45°C. When addition is complete, heat the mixture on the steam bath to 70-80°C, while stirring, for 1 hour. Cool the mixture to room temperature, and acidify to pH 1 with 3 M sulfuric acid (16 mL of concentrated acid cautiously added to 84 mL of cold water). Add solid sodium bisulfite, while stirring, until a colorless solution is produced. Wash the solution into the drain with water.7... 

Wear eye protection, laboratory coat, and rubber gloves. Dissolve the aniline (1 mL) in 50 mL of 3 M sulfuric acid (prepared by slowly adding 8 mL of concentrated sulfuric acid to 21 mL of water). Weigh 10 g of potassium permanganate and stir small portions of the solid into the aniline solution over a period of about 1 hour. Stir the mixture at room temperature for 48 hours, and then neutralize the solution by adding solid sodium carbonate or a 10% solution of sodium hydroxide. Add solid sodium bisulfite until solution is colorless. Decant the clear liquid into the drain and discard any brown solid with regular refuse.11,12... 

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