Toluene ozonide

Toluene Ozonide. Colorl crysts or glutinous mass stable at 0° but decompd at 8° extremely expl. First prepd in 1891 by Dieckhoff Ref C.D. Harries et al, Ann 343,314 (1905)... 

Thermal decomposition of allylbenzene ozonide (58) at 37°C in the liquid phase gave toluene, bibenzyl, phenylacetaldehyde, formic acid, (benzyloxymethyl)formate, and benzyl formate as products. In chlorinated solvents, benzyl chloride is also formed and in the presence of a radical quench such as 1-butanethiol, the product distribution changes. Electron spin resonance (ESR) signals are observed in the presence of spin traps, adding to the evidence that suggests radicals are involved in the decomposition mechanism (Scheme 9) <89JA5839>. 

An important paper by Salomon, Clennan and coworkers on dialkyl peroxides , where also one ozonide was reported, appeared in 1985. In this paper, a correlation among and 0 chemical shifts was established, and the influence of several factors like concentration, temperature, solvent and, naturally, chemical structure was thoroughly studied but confined to dialkyl peroxides. There was a gap of several years before the appearance of a further note reporting data of seven 1,2,4-trioxolanes (ozonides), 1-4, and of the 1,2,4,5-tetroxane 5. Their 0 NMR data are given in Table 2. Spectra were obtained at natural isotopic abundance, in toluene at 27 °C. 

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