1129-40-4Relevant academic research and scientific papers
Disproportionate Coupling Reaction of Sodium Sulfinates Mediated by BF3·OEt2: An Approach to Symmetrical/Unsymmetrical Thiosulfonates
Cao, Liang,Luo, Shi-He,Jiang, Kai,Hao, Zhi-Feng,Wang, Bo-Wen,Pang, Chu-Ming,Wang, Zhao-Yang
supporting information, p. 4754 - 4758 (2018/08/24)
The BF3·OEt2-mediated disproportionate coupling reaction of sodium sulfinates was found for the first time. In this reaction, various S-S(O)2 bonds can be formed, efficiently giving thiosulfonates in moderate to excellent yields. As a convenient protocol for the synthesis of symmetrical and unsymmetrical thiosulfonates, its reaction mechanism involves the formation of a thiyl radical and sulfonyl radical via a sulfinyl radical disproportionation. What is more, this transformation can also be applied practically as a gram-scale reaction and to the two-step synthesis of sulfone and sulfonamide in one pot in situ using thiosulfonate as an intermediate.
Selective Oxidation of Unsymmetrical Thiosulfinic S-Esters to the Corresponding Thiosulfonic S-Esters with NaIO4
Takata, Toshikazu,Kim, Yong Hae,Oae, Shigeru
, p. 1443 - 1447 (2007/10/02)
Unsymmetrical thiosulfinic S-esters were oxidized with sodium metaperiodate in aqueous media to the corresponding unsymmetrical thiosulfonic S-esters nearly quantitatively.The oxidation was accelerated by addition of a catalytic amount of inorganic and organic acids or halogen.Sulfinic esters were produced competitively along with the thiosulfonic S-esters in the oxidation of thiosulfinic S-esters in aqueous alcohol.However, unsymmetrical disulfides were not oxidized selectively to the corresponding unsymmetrical thiosufonic S-esters but a mixture of the both symmetrical and unsymmetrical thiosulfonic S-esters was obtained.
