Thionosulfite intermediates in sulfur extrusion

ORGN 571

Nicolas Eghbali, nicolas.eghbali@mcgill.ca and David N. Harpp, david.harpp@mcgill.ca. Department of Chemistry, McGill University, Otto Maass Building, 801 Sherbrooke Street West, Montreal, QC H3A 2K6, Canada
Over fifty years ago, Foss postulated that a branched-bond sulfur structure might play an important role as an intermediate in the extrusion or insertion of sulfur atoms. Studies on the sulfur monofluoride structure in 1964 and the discovery of thionosulfites further supported the existence of branched-bond sulfur compounds. By converting the cyclic dialkoxy-disulfide 1 to its structural thionosulfite isomer 2, we have brought a strong chemical demonstration that the branched-bond sulfur species can be involved in sulfur extrusion. Further investigations show the existence of an equilibrium between thionosulfite 2 and sulfoxylate 3.