Substituted Dibenzothiophenes I: Synthesis, Chromatography, Mass Spectrometry and Structure Elucidation by1H NMR Spectroscopy

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Abstract
Some polychlorinated and polymethylated dibenzothiophenes have been synthesized to serve as model compounds in environmental analysis. In order to obtain pure isomers, the synthesis mixtures have been fractionated with reversed-phase high performance liquid chromatography. In spite of a high sensitivity, mass spectrometry does not provide any reliable way to determine the precise structures of different isomers. Therefore, 1H NMR spectroscopy has been utilized as an aid in their analysis. The structures for two isomeric tetramethyldibenzothiophenes could be suggested on the basis of their 1H NMR spectra. Also some proposals for possible structures of two isomeric trimethyldibenzothiophenes and two fractions of chlorinated dibenzothiophenes are given. More structural isomers, however, need to be prepared for their unique structure determinations.