Ozonides ozone adducts

Solid styrene was exposed at — 196°C to ozone, in an attempt to discern whether the behavior of the system is similar to that of olefinic compounds, yielding an ozonide, or to that of aromatic compounds, yielding a 7r-complex. On heating to about — 100°C, an adduct is formed that is stable until about —55 °C, when benzaldehyde and a peroxidic polymer are slowly obtained. The structure of the adduct is probably that of a POZ, based on the similarity of the IR spectrum with the ozone adduct of vinyl chloride described in the preceding paragraph . 

IR spectrophotometry, 661, 662 TEARS assay, 667 hydroperoxide oxidation, 692 Upid hydroperoxides, 977-8 decomposition, 669 DNA adducts, 978-84 protein adducts, 984-5 ozone adducts, 734 ozonide reduction, 726 ozonization characterization, 737, 739 peroxydisulfate reactions, 1013, 1018 Alkali metal ozonides, 735-7 Alkaline peroxide process, pulp and paper bleaching, 623... 

Diazene, furan ozonide decomposition, 730 Diazo compounds, ozone adducts, 734 Diazonium salts, TEARS assay, 667 Dibenzoyl peroxide, determination, 698 Z-Dibenzoylstilbene, tetracyclone bleaching, 734-5... 

B. Primary Ozonides and Adducts of Ozone with Aromatic... 

When the solvent is or contains an alcohol, it is often incorporated in the ozonation products. For example, Kratzl et al. (1976) obtained about one mole of ethyl formate per mole of veratrole ozonized when the solvent was 10% ethanol in chloroform. Tanahashi et al. (1975) obtained methyl esters and, on hydrogenolysis of some ozonide/methanol adducts, methyl benzyl ethers using... 

The yield data in Figures 3 and 4 can be rationalized on similar grounds. In the cis case the initial olefin-ozone adduct can be diverted to 3-heptene ozonide by butyraldehyde, and by doing so can eliminate a precursor to 3-hexene ozonide. This process continues to operate throughout a wide range of aldehyde concentrations with the total ozonide... 

The fate of 0 (if it is ever produced in natural waters corresponding to OH) is transformation into the ozonide anion under oxide conditions (5.127), which is an important intermediate in alkaline solution with a lifetime of about 10 s. Ozonide anion (not to be mixed up with the olefin-ozone adduct. Chapter 5.7.4) is easily produced through electron transfer onto dissolved ozone the electron affinity of O3 is several times (2.1 eV) that of O2 (0.44 eV Pichat et al. 2000, Addamo et al. 2005). 

Ozone and singlet oxygen add to the benzvalene double bond to form the corresponding ozonide and 1,2-dioxetane adduct respectively with retention of the bicyclobutane part (86)79). 

Singlet oxygen2 (see also Triphenyl phosphite ozonide, this volume). Dilute methylene chloride solutions of this reagent (1) react quantitatively at—78° with one equivalent of ozone to give the 1 1 adduct (2).s The adduct decomposes at room temperature to the phosphate (3) with evolution of singlet oxygen as shown... 

Further cycloadditions include the 1,3-dipolar cycloadditions as well as the respective [2-i-l]-reactions. The latter have already been mentioned in the reaction of carbenes photochemically generated from diazirines (Section 6.5.2.4). Experimental examples for [3-i-2]-cycloadditions have not yet been reported. Still theoretical considerations gave rise to the assumption that such reactions with, for example, azides, diazomethane or other classical 1,3-dipoles should readily take place on the surface dimers. The calculations further revealed that the cleavage of nitrogen under formation of the respective azacyclopropane as known for normal alkenes should also take place for the [3-i-2]-adducts bound to diamond. For the reaction with ozone (Section 6.5.2.3) it has not yet been clarified whether or not an ozonide is initially formed by [3-i-2]-cycloaddition, only then to be transformed into the carbonyl compound. 

Phosphines and phosphites are readily oxidized by ozone (81). The 1 1 adducts have pentacovalent phosphorus structures (82). Ozonides are reductively cleaved by triphenylphosphine (83). 

---