Ozonides, detection

Significant advances in the chemistry of these ring systems over the past 10 years include the first unambiguous detection, and characterization by microwave spectroscopy as 1,2,3-trioxolane, of the primary ozonide from ethene and ozone (cf. Section 4.15.3.2), and the introduction of 1,3,2-dioxathiolane 2,2-dioxides as epoxide equivalents in organic synthesis (cf. Section 4.15.5.3). Advances have also been made in the synthesis and characterization of the chemistry of 1,2,3-trithiolanes and 1,2,3-trithioles. 

Environmental Protection Agency (USA) emergency response guidebook electron spin resonance field desorption mass spectrometry flow injection analysis flame ionization detection/detector fluorescence detection/detector Xylenol Orange-ferric complex final ozonide... 

Cyclohexene, primary ozonide, 720 Cyclohexyl hydroperoxide, flame ionization detection, 689 Cyclopentadiene... 

Ethyl 10-undecenoate ozonide was autoxidized at 95% in the absence of a catalyst. Diethyl sebacate, methyl ethyl sebacate, and dimethyl sebacate were detected after diazomethane treatment. When the ozonide was oxidized in acetone over platinum black and similarly treated with diazomethane, dimethyl sebacate could not be detected. 

The ozonide (4.3 grams) in ethyl acetate (25 ml.) was shaken with reduced platinum oxide (approximately 50 mg.) in a Burgess-Parr apparatus containing oxygen at 50 p.s.i.g. for 24 hours. The solution was aldehyde-free and gave a negative peroxide test. There was no detectable... 

Since each ozonide exists as a pair of cis-trans isomers, six isomeric ozonides can be detected in such cases. 

We were unable to detect an intermediate [e.g., Criegee s primary ozonide (9)] by low temperature NMR (to — 130°C) yet the above-mentioned results and the fact that IV does not react with Feist s ester strongly suggest that a highly reactive intermediate does exist. 

Greenwood91,92 demonstrated the formation of primary ozonides in the reaction of some reaction with liquid ozone gave products that formed glycols on mild reduction with isopropylmagnesium bromide. On the other hand, primary ozonides have not been detected with certainty in the case of cis-olefins.88 91 The reaction of cis-3-hexene,93 eis-2-butene, cis-2-pentene, and ethylene92 with ozone at —112° in pentane led to extremely explosive substances, which could be primary ozonides. In the... 

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