Ozonolysis mechanism, review

The development of ideas about ozonolysis and its mechanism has been reviewed. It is not an extensive review about ozone chemistry or ozonolysis reactions, but it highlights how the rational process was developed and how conclusions were drawn at a time when limited instrumental facilities were available. Several ideas and assumptions that were made to understand the chemical properties of the ozone molecule and the ozonolysis mechanism have been discussed. ... 

The ozonolysis of alkenes has been comprehensively covered in several excellent reviews (see Section 4.16.1) and will therefore not be discussed in detail here. It is pertinent, given the importance of 1,2,4-trioxolane synthesis, to highlight the key points of the ozonolysis reaction mechanism and several other developments. 

The reactions of O3 with C3H6, 9 and 10, were based on a review of the mechanism of ozonolysis by Murray (15). The accepted mechanism in the gas phase is similar to that commonly referred to as the Criegee mechanism in the liquid phase. The attack of O3 on C3H6 is electrophilic, and Vrbaski and Cvetanovic (16) have correlated the electrophilic behavior with that of oxygen atom-olefin reactions. Both reaction rates correlate with the ionization potentials of a series of olefins. 

Ethene, like other alkenes, reacts also with ozone in the atmosphere. The older work on ozone reactions has been reviewed by Leighton (1961) and by Bufalini and Altshuller (1965). More recent work has done much to clarify the principal reaction mechanisms involved. Criegee (1957, 1962, 1975), who had studied the ozonolysis of alkenes in solution, suggested that ozone adds to the C=C double bond, forming an unstable intermediate, which then decomposes toward a carbonyl compound and a zwitterion fragment, for example ... 

The goals set with respect to the spectroscopy and kinetics of the simple peroxy radicals was mainly achieved. A detailed review on the chemistry and role of the peroxy radicals in the photo-oxidation of VOC was written within the LACTOZ project [25]. Further studies on quantum yields determination of photolabile carbonyl compounds and on the mechanism of the ozonolysis of alkenes are required. 

A review of mechanisms of ozonolysis of unsaturated carbonyl compounds and alcohols has addressed effects of the substrate structure and reaction conditions on the product composition. " ... 

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