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Three-membered benzylic thia-rings of polycyclic aromatic hydrocarbons: synthesis, molecular calculations and properties

In cancer research/organic synthesis related studies, several hitherto unknown three-membered benzylic thia-ring-containing polycyclic aromatic hydrocarbons, PAH-episulfides (PeSs) and PAH diol episulfides (DeSs), have been synthesized and their relevant chemistry explored. These compounds represent the sulfur analogs of the corresponding diol epoxide carcinogens. A highly efficient general synthetic methodology has been developed for the conversion of epoxides and, stereoselectively, diol epoxides into their corresponding episulfides using the nucleophilic sulfur transfer agent DMTF. The newly-synthesized DeSs show remarkable stability towards aqueous acid whereas both PeSs and DeSs are thermodynamically unstable (loss of sulfur)—consistent with the predictions of previously performed molecular orbital calculations. This review constitutes an account of what has been achieved in this area, focusing on aspects related to cancer research and the implications for further research.