Determination of Arene Oxides by a Gas Chromatography-Mass Spectrometry System: Thermal Reactions of 9, 10-Epoxy-9, 10-Dihydrophenanthrene

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Abstract
An analytical technique involving the use of a gas chromatograph coupled to a mass spectrometer-computer system, has been developed to detect arene oxides using 9, 10-epoxy-9, 10-dihydro-phenanthrene as a model substrate. The gas chromatograph was equipped with a hydrogen flame ionization detector and a high-resolution glass capillary column coated with SE-52 (methyl phenyl silicone). Two simultaneous thermal reactions (deoxygenation and rearrangement) of 9, 10-epoxy-9, 10-dihydrophenanthrene in the gas chromatograph were observed. The method developed was compared with a conventional method utilizing a packed glass column. Under the latter conditions neither thermal reactions nor 9, 10-epoxy-9, 10-dihydrophenanthrene were detected. The identification of the reactant and products was achieved by comparison of retention times and mass spectral fragmentation patterns obtained from authentic samples.