Ozonides with silver oxide

The oxidative decomposition of ozonides is further accomplished by their treatment with hydrogen peroxide [97] in the presence of formic acid [95, 99] or acetic acid [102, 103] or with silver oxide and nitric acid [77] (equations 109-112). 

Compound A, Ci2H2aN2f was soluble in dilute acid, but did not react with benzenesulfonyl chloride. Upon addition of excess methyl iodide, Compound A reacted. It was then treated with silver oxide, and the resulting product heated. Thus B, CaHii, was formed. B was treated with ozone and the ozonide decomposed with dilute acid in the presence of zinc... 

The oxidative cleavage of ozonides leads to carboxylic acids. This cleavage is carried out by treatment of the crude ozonization product with alkaline silver oxide, potassium permanganate, or hydrogen peroxide solution,121 or with peracetic acid.122... 

The literature of this reaction to 1940 has been adequately reviewed. The emphasis up to that time was placed on obtaining higher yields of carbonyl compounds by hydrolysis of the ozonides. Several methods have been described for the oxidative cleavage of ozonides to acids. These procedures may prove valuable in the synthesis of certain acids. By adding the ozonide of 1-tridecene to an alkaline silver oxide suspension at 95°, a 94% yield of lauric acid is obtained. Decomposition of ozonides with 30% hydrogen peroxide is described for the preparation of 5-methyl-hexanoic acid (67%) from 6-methyl-l-heptene and of adipic acid (60%) from cyclohexene. A study of solvents for ozonolysis has been made. ... 

The oxidative workup used to produce acids from ozonides such as 349 uses reagents such as hydrogen peroxide, peroxy acids, silver oxide, chromic acid or permanganate. The conversion of cyclohexene to adipic acid by treatment with (1) O3 and (2) H2O2 is a simple example of a typical oxidative workup. When the ozonide is disubstituted (two carbon groups on the initial carbon of the alkene), the product is a ketone and... 

Only fluorine, atomic oxygen and FgO have higher redox potentials. The gas oxidises moist sulphur to jH2S04, raises silver(I) compounds to the 2 state and converts olefinic compounds to ozonides. The reaction 2O3 -> SOg, which is catalysed by many metals and metal oxides, is exothermic and rapid above 200°. Gaseous ozone is deeper blue than oxygen it condenses at — 112° to a dark blue liquid which freezes at —193° to a dark purple solid. Surprisingly, the liquid is not completely miscible with liquid oxygen. 

Ethylene forms explosive mixtures in air the LEE and UEL values are 2.7% and 36% by volume of air, respectively. Its reaction with fluorine is explosively violent (AH = —112 kcal/mol), and violent with chlorine (AH = —36 kcal/mol). In the presence of sunlight or UV light, an ethylene-chlorine mixture will explode spontaneously. The reaction is explosive at room temperature over the oxides of mercury or silver (Mellor 1946, Suppl. 1956). Ethylene reacts vigorously with oxidizing substances. It reacts with ozone to form ethylene ozonide, H2C(03)CH2, which is unstable and explodes on mechanical shock. Acid-catalyzed addition of hydrogen peroxide may produce ethyl hydroperoxide, which is unstable and explodes on heat or shock ... 

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