Development of Odorless Sulfur Reagents and Their Applications

Abstract

Development of odorless thiols [1-dodecanethiol (Dod-SH), 4-trimethylsilylphenylmethanethiol (TMSBM), 4-trimethylsilylbenzenethiol (TMSBT), and 6-morpholinohexanethiol (MHT)] and odorless sulfides [dodecyl methyl sulfide (Dod-S-Me), methyl 6-morpholinohexyl sulfide (MMS)] and their sulfoxides [dodecyl methyl sulfoxide (Dod-S (O) -Me), methyl 6-morpholinohexyl sulfoxide (MMSO)] as odorless substitutes for the foul-smelling ethanethiol, benzyl mercaptan, benzenethiol, and dimethyl sulfide (DMS) is described. They are conveniently applied for dealkylation, thiol exchange reaction, reductive ozonolysis, Corey-Kim oxidation, Swern oxidation, hydroboration, and reduction. The products of these reactions utilizing morpholine based thiol MHT, sulfide MMS and its sulfoxide MMSO can be easily purified by only acid-base extraction without involving chromatography, thereby eliminating unpleasant odors, saving time and protecting the environment. In view of current environmental and economic factors, the utility of these simple reagents could be enormously beneficial.