The first exclusive regioselective fragmentation of primary ozonides controlled by remote carbonyl groups on ozonolysis of norbornene derivatives and reaction of final ozonides with triethylamine as a new probe for determining the regiochemistry of carbonyl oxide formation from primary ozonide fragmentation are reported. Ozonolysis of the endo adducts 3a-d and the deuterated compounds 8a and 8b...

Key words ozonolysis - photoexcitation alkenes selectivity nitroarenes

Ozone toxicity in the lung is thought to be mediated by products derived from the reaction of ozone with components of the lung epithelial lining fluid. Cholesterol is an abundant component of this epithelial lining fluid, and it is susceptible to ozonolysis, yielding several stable products including 3beta-hydroxy-5-oxo-5,6-secocholestan-6-al and 5beta,6beta-epoxycholesterol. Both 5beta,6beta-...

New particle formation during the oxidation of αand β-pinene (C10H16) by ozone, OH and NO3 was studied by measuring the particle size distributions with a scanning mobility particle sizer (TSI 3936). The results indicate a drastically higher nucleation potential of the ozonolysis than in the reaction with either OH or NO3. On the contrary, the contribution of the individual oxidation reactions ...

Green leaf volatiles (GLVs) are a class of woundinduced volatile organic compounds emitted by several plant species. Turf grasses emit a complex profile of GLVs upon mowing, as evidenced by the “freshly cut grass” smell, some of which are readily oxidized in the atmosphere to contribute to secondary organic aerosol (SOA). The contribution of lawn-mowing-induced SOA production may be especially ...

The recently developed technique of field-induced droplet ionization (FIDI) is applied to study interfacial chemistry of a single droplet. In a new variation of the FIDI method, 1-2-mm-diameter droplets hang from a capillary and undergo heterogeneous reactions between solution-phase analytes and gas-phase species. Following a specified reaction time, the application of a high electric field ind...

Ozonolysis is one of the dominant oxidation pathways for tropospheric alkenes. Although numerous studies have confirmed a 1,3-cycloaddition mechanism that generates a Criegee intermediate (CI) with form R1R2COO, no small CIs have ever been directly observed in the ozonolysis of alkenes because of their high reactivity. We present the first experimental detection of CH2OO in the gas-phase ozonol...

Photolysis of alkene-terminated self assembled monolayers (SAM) deposited on Degussa SiO(2) nanoparticles is studied following oxidation of SAM with a gaseous ozone/oxygen mixture. Infrared cavity ring-down spectroscopy is used to observe gas-phase products generated during ozonolysis and subsequent photolysis of SAM in real time. Reactions taking place during ozonolysis transform alkene-termin...

This account describes the development of methodologies for ‘reductive’ ozonolysis, the direct ozonolytic conversion of alkenes into carbonyl groups without the intermediacy of 1,2,4-trioxolanes (ozonides). Ozonolysis of alkenes in the presence of DMSO produces a mixture of aldehyde and ozonide. The combination of DMSO and Et3N results in improved yields of carbonyls but still leaves unacceptab...