The Research About The Synthesis Methodology Of Thiosulfonates And Disulfides

Organic sulfur compounds are a sort of compounds with excellent performance.Nowadays,they are widely used in medicine,polymer materials,photographic processes,lubricant,food additives and other fields.Among various organosulfur compounds,thiosulfonates and disulfides are of particular interest with many unique properties.However,there is barely a synthetic method which could handle with simple operations,facile materials,mild condition,widely substrates scope and high yields.In order to efficiently and succinctly prepare these compounds,we developed a feasible synthetic route through experiments.By appropriate choice of the solvents,these two types of useful compounds were prepared.The reaction of sulfonyl chlorides and tetrabutylammonium iodide in CH3CN:Acetone?5:1?and DMF respectively gave thiosulfonates and disulfides in good to excellent yields.We used sulfonyl chlorides as starting materials,CH₃CN/Acetone?5:1?as the reaction solvent to form 25 examples of symmetrical thiosulfonates and 5 examples of unsymmetrical thiosulfonates in 56-93% yields.Moreover,the use of DMF as the reaction solvent generated 26 examples of symmetrical disulfides and one example of unsymmetrical disulfide in 43-93% yields.Compared with the existing synthetic methods,the protocol has some advantages: innovative,tunable,readily available starting materials,higher yield,mild reaction conditions,room temperature,wide substrate scope,high chemoselectivity.This research complies with the principles of green chemistry.These transformations probably proceeded through a reducing-coupling pathway.