From ozonides

Dichloroaluminium hydride in ether or sodium borohydride in TEA can lead to formation of ethers from ozonides by reductive cleavage of the two C—O bonds of the peroxide bridge (Equation (19)) <85JOC275>. 

Peroxides can be obtained from ozonides in various ways. Dioxirane (246), the simplest cyclic peroxide, appears in the microwave spectrum of ethylene-ozone mixtures, in the — 115 to — 110 °C temperature range, probably as a decomposition product of the primary... 

NOC1 and an alcohol 9-9 From ozonides 9-10 Oxidative cleavage of enol ethers 9-13 Reaction between carboxylic acids and lead tetraacetate 9-18 Oxidation of ethers 9-22 Oxidation of primary alcohols or aldehydes... 

Hydrogen atoms in allylic position are favorite sites for hydroperoxidation of chains. So, this mechanism proceeds in the formation of lateral hydroperoxides, and not like for other polymers, in intramolecular peroxides. Rearrangement of chemical structures coming from ozonides are rapidly observed (Scheme 33). 

A stable ozonide of an arene. Ozonolysis of the cyclopentophenanthrene 1 leads to an ozonide (2) that is stable in the dark at 20° for several weeks. The ozonide is also unusual in that it is converted into 3 and 4 in high yield products of this type are not usually formed from ozonides. 

Scheme 5. Mechanism of the formation of an addition product form switterion or from ozonide and PD accounting for the polymer-bound moiety.

Aldehydes can be obtained homogeneously from ozonides by reductive cleavage, which can be effected either by zinc in glacial acetic acid or by catalytic hydrogenation of the ozonide118,119 in the presence of a 1 19 palladium-calcium carbonate catalyst.120 Adipdialdehyde has thus been obtained from cyclohexene in 60-70% yield 121... 

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... 

Dimethyl sulfoxide Aldehydes and carboxylic acids from ozonides... 

Without additional reagents Acoxyketones from ozonides Thermal rearrangement... 

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