Uses
Trimethylene Di(thiotosylate) is used as a reactant in the enantioselective total synthesis of (-)-O-methylpallidinine, which is a naturally occurring morphinan alkaloid.
Reactions
1,3-Propanedithiol Bis(p-toluenesulfonate) could be used in the below reactions:
dithianylation and dithiolanylation of methylene groups adjacent to carbonyl; α,α-dithianyl cycloalkanones undergo oxidative ring scission; oxidation of ketones to 1,2-diketones can be achieved by α,α-dithianylation or dithiolanation of ketones followed by hydrolysis.
Synthesis
Treatment of potassium thiotosylate, itself made by the reaction of p-Toluenesulfonyl Chloride with Potassium Hydrogen Sulfide, with 1,3-dibromopropane or 1,2-dibromoethane in the presence of Potassium Iodide affords 1,3-propanedithiol bis(p-toluenesulfonate) and 1,2-ethanedithiol bis(p-toluenesulfonate), respectively.
