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Abstract Since its introduction comprehensive two-dimensional gas chromatography (GC × GC) has been widely applied to analyze complex samples due to its enhanced peak capacity and selectivity, thereby increasing the number of identifiable peaks and improving coelution issues. Even though it is still undergoing development, GC × GC provides many advantages in the analysis of petroleum-derived samples, whether in reservoir geochemistry applications or in environmental studies associated with spilled oils. In general, it facilitates more thorough fingerprinting and compositional evaluation. In environmental studies, it helps enhance understanding of weathering processes and the environmental behavior of hydrocarbons, as its chromatographic retention indices can robustly estimate liquid vapor pressures, aqueous solubility and other physical chemical properties. This review presents a brief history of GC × GC instrumentation, discussing recent and significant advances in petroleum applications, from data handling techniques to reservoir geochemistry and environmental forensics, as well as some specific advantages achieved and certain limitations that continue to be encountered. [ABSTRACT FROM AUTHOR]

The assignment of the diazo site in products of the reaction of p-toluenesulfonylhydrazine with beta-lapachone, 3,4-dihydro-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5,6-dione, and other 1,2-naphthoquinones in methanol solution at room temperature has been accomplished using 1H,13C HMBC and 1H,15N HMBC NMR experiments. Only one diazo-naphthalenone product was isolated in yields ranging from 50-100% from each reaction. The site of diazo substitution of beta-lapachone and derivatives is the 1-position, in contrast to substitution at the 2-position in 4-MeO-1,2-naphthoquinone. Steric factors, rather than electronic factors, control the reaction site. Along with 2-diazo-1(2H)-naphthalenone, an additional product isolated from the reaction of p-toluenesulfonylhydrazide with 1,2-naphthoquinone was 2-diazo-4-hydroxy-1(2H)-naphthalenone. Confirmation of the formation of 6-diazo-2,2-dimethyl-2,3,4,6-tetrahydro-2H-benzo[h]cromen-5-one, obtained from beta-lapachone, was achieved using single crystal X-ray diffraction., (2006 John Wiley & Sons, Ltd.)