Potassium permanganate and sodium periodate

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 mixture of potassium permanganate and sodium periodate has also been used to cleave double bonds. This procedure, usually referred to as the Lemieux-von Rudloff reaction, can be carried out in several mixed solvent systems such as butanol and water, dioxane and water " or acetone and water. " It has also been claimed that the addition of phase transfer agents improves yields. 

Undecylenic acid (10-undecenoic acid), when treated with potassium permanganate and sodium periodate in an aqueous solution of potassium carbonate at 20 °C for 20 h, gives sebacic acid (decane dioic acid) in 73% isolated yield [763]. A similar oxidation of oleic or elaidic acid yields a mixture of pelargonic acid and azelaic acid [763] (equation 474). 

The periodate-permanganate method used was based on a method described previously [105], but three changes from the original published procedure were found to be necessary. A sample size of 50 mg was taken for all oxidations. The same quantities of oxidant, potassium carbonate, and sodium bisulfite (26 ml, 45 mg, 1.06 g, respectively) were used for all samples. An inert marker (5 mg) of methyl palmite or stearate was added to all samples prior to oxidation to serve as a rough check on the completeness of oxidation and the recovery of fragments. 

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 ... 

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... 

Hydroxy carboxylic acids and their esters are oxidized to keto acids and their esters, respectively. o-Nitromandelic acid is oxidized to o-nitro-phenylglyoxylic acid with a dilute solution of potassium permanganate at room temperature in 54% yield [886], The oxidation-of ethyl 3-hydroxy-cyclobutanecarboxylate with ruthenium tetroxide and sodium periodate in... 

Oxidation of cyclopropenes by osmium(VIII) oxide and sodium periodate, by potassium permanganate or by ozone normally gives 1,3-diketones, although in some cases further reactions occur. Examples are the reaction of 7 with osmium(VIII)oxide " 8, " and with... 

Introduction. Sodium periodate is widely used for the oxidation of a variety of organic substrates and as a cooxidant in other oxidation reactions (see Sodium Periodate-Osmium Tetroxide and Sodium Periodate-Potassium Permanganate) f The Nal04 oxidation is usually conducted in water however, for organic substrates that are insoluble in water, an organic cosolvent (e.g. MeOH, 95% EtOH, 1,4-dioxane, acetone, MeCN) is used. Alternatively, the oxidation can be conducted either with phase-transfer catalysis (PTC) using quaternary ammonium or phosphonium salts in a two-phase system, or in an organic solvent if the oxidant is first coated on an inert support. ... 

The residue is treated with 0.6 ml. of dioxane, 0.2 ml. of 0.1 N potassium permanganate, and 0.25 ml. of 0.01 N periodic acid and is allowed to stand at room temperature for 15 minutes. If the permanganate color disappears, additional 0.1 ml. portions of this reagent are added. The reaction mixture is transferred quantitatively to a small separatory funnel with about 10 ml. of water and 30 ml. of benzene and the mixture is thoroughly shaken. After discarding the aqueous layer, the benzene phase is washed once with 10 ml. of freshly prepared sodium dithionite solution and then with three 10 ml. portions of water. After removal of the solvent under reduced pressure at a temperature below 60 °C. the residue is ready for polarography. 

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... 

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°. 

Some of the investigations carried out in the first half of the twentieth century were related to CL associated with thermal decomposition of aromatic cyclic peroxides [75, 76] and the extremely low-level ultraviolet emission produced in different reaction systems such as neutralization and redox reactions involving oxidants (permanganate, halogens, and chromic acid in combination with oxalates, glucose, or bisulfite) [77], In this period some papers appeared in which the bright luminescence emitted when alkali metals were exposed to oxygen was reported. The phenomenon was described for derivatives of zinc [78], boron [79], and sodium, potassium, and aluminum [80]. 

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 ... 

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). 

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