Synthesis of a bis-Thiol Receptor for Arsenic(III) Compounds.

摘要

The effects of ingesting trivalent and pentavelent arsenic compounds range from developmental problems to death. They dissolve readily in water, and more of these compounds are finding their way into groundwater due to agricultural runoff, leeching from preserved wood and mining, among other sources. Development of an easily visualized molecule that binds selectively and strongly to arsenic compounds might allow ease of both the removal and detection of these contaminants from water. The program HostDesigner was used to design a receptor containing thiol groups that would favorably bind to an arsenic(III) compound. The precursor to this receptor is a a novel dihydrodimethylisobenzofuran-diol that was synthesized via a Diels-Alder reaction followed by oxidative cleavage and then NaBH4 reduction to the diol. Starting from o-Bromofluorobenzene and 2,5-Dimethylfuran, cis-1,3- bis-Hydroxymethyl-1,3-dimethyl-1,3-dihydroisobenzofuran was obtained in 10% yield. Methods to convert the diol to a dithiol were explored, including a thio-Mitsunobu reaction.