A novel synthesis of organic diselenapolysulfides

Selenium‐Containing Tetrachalcogenins and Pentachalcogenepins Fused to Aromatic Systems

“…During purification and NMR spectroscopic measurements in solution, all cyclic polychalcogenides, except benzotrichalcogenoles, slowly deposited elemental selenium, which has been reported to be characteristics of labile selenium compounds. [10,19] Five-membered polychalcogenides are the most stable compounds and environmental factors such as heat, light, air, and polar solvents do not interfere with the ring systems. Phenathro [9,10- (18) was also found to be a stable product under all experimental conditions.…”

“…Many authors also experienced similar results concerning the handling of labile selenium compounds. [10] Several attempts by other methods also did not give either target product 1 or 2 ( Figure 1). The sulfur source was also changed from S 8 to S 2 Cl 2 in the presence or absence of a Lewis acid catalyst at low tempera-ture, but stable products were still not isolated.…”

“…[8] Seven-mem-bered multichalcogen compounds are also intriguing due to the rich chalcogen chemistry associated with the flexible Se-S bond and intramolecular ring rearrangement through selenium extrusion Ϫ these compounds are important for their inherent stability. [4,10] Although there is only one report about the formation of BTTT, [6a] the similar six-membered benzopolychalcogenide containing selenium has never been reported. It is well known that the C-Se bond is stronger than the S-Se or Se-Se bonds.…”

“…It is well known that the C-Se bond is stronger than the S-Se or Se-Se bonds. [10] Therefore, the syntheses of cyclic benzopolychalcogenides 1-4 ( Figure 1) were attempted with the intention to build upon the aromatic systems to develop compounds that contain one or more selenium atoms directly bonded to the aromatic carbon atoms. The intrinsic and extrinsic nature of these cyclic polychalcogenides as influenced by the fused aromatic rings still remains to be studied.…”

New Sulfenyl Chloride Chemistry: Synthesis, Reactions and Mechanisms toward Carbon-Carbon Double Bonds

“…Recently, we discovered [110] that sulfenyl chloride 2 (or its thio 3 or dithio 4 homolog) reacts smoothly under mild conditions with symmetric diselenides 93 affording polychacolgenides 94-96 as the main products, respectively. The reactions are generally very rapid and the procedure was optimized according to temperature, solvent and molar ratio of the substrate in order to maximize the yield of polychacolgenides 94-96 (Table X) 95a; R = CH 3 95b; R = C 6 H 5 CH 2 95c; R = C 6 H 5 96a; R = CH 3 96b; R = C 6 H 5 CH 2 96c; R = C 6 H 5…”