Ozonide ions with alkenes

Reactions of 07 with Alkanes and Alkenes. Ozonide ions are intermediate in reactivity between 0 and 01 (20,21). On MgO they re-... 

Alkanes—Continued reactions—Continued with ozonide ions, 135 with superoxide ions, 134-35 role of oxygen ions in oxidation. 138-41 Alkenes, reactions with oxygen ions, 134 with ozonide ions, 135 with superoxide ions, 134-35 Aluminosilicate gels, alkali cations, 241... 

Ozone is a strong oxidizing agent. Its concentration can be determined by reacting it with iodide ions and titrating the iodine formed with standard sodium thiosulfate(VI). It forms ozonides with alkenes. See ozonolysis. 

This indicates no evidence of stereorandomization about the carbon—carbon double bond. It means that 74 cleaves in a concerted fashion to yield syn and anti zwitter-ions produced in different amounts depending on the alkene geometry. The stereo-isomeric zwitterions remain attached to each other like an ion pair and recombine stereoselectively with aldehydes. The subtle nature of ozonation, however, may be illustrated by the observation that ozonide formation may be nonconcerted under... 

The mechanism of the reaction of ozone with double bonds (equation 68) is very complex and still subject to arguments. An alkene and ozone may first form a it complex (a), which forms a a complex (b), a molo-zonide (c), or both. The molozonide may change to a dipolar ion (d), which breaks down with the fission of the carbon-carbon bond to a carbonyl compound and another dipolar ion (e). The two species recombine to give the ultimate product, ozonide (f) (1,3,4-trioxolane, also known as 1,3,4-trioxacyclopentane) [76], The temporary presence of the carbonyl com-... 

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