6829-66-9Relevant articles and documents
Direct conversion of sulfinamides to thiosulfonates without the use of additional redox agents under metal-free conditions
Ji, Yuan-Zhao,Li, Hui-Jing,Wang, Jun-Hu,Wu, Yan-Chao,Zhang, Chi
, p. 9291 - 9298 (2021/11/13)
Direct conversion of sulfinamides to thiosulfonates is described. Without the use of additional redox agents, the reaction proceeds smoothly in the presence of TFA under metal-free conditions. This protocol possesses many advantages such as odourless and stable starting materials, broad substrate scope, selective synthesis, and mild reaction conditions. This journal is
Visible-Light-Accelerated C?H Sulfinylation of Heteroarenes
Meyer, Andreas Uwe,Wimmer, Alexander,K?nig, Burkhard
supporting information, p. 409 - 412 (2016/12/30)
Heteroaromatic sulfoxides are a frequent structural motif in natural products, drugs, catalysts, and materials. We report a metal-free visible-light-accelerated synthesis of heteroaromatic sulfoxides from sulfinamides and peroxodisulfate. The reaction proceeds at room temperature with blue-light irradiation and allows the C?H sulfinylation of electron-rich heteroarenes, such as pyrroles and indoles. An electrophilic aromatic substitution mechanism is proposed based on the substrate scope, substitution selectivity, and competition experiments with different nucleophiles.
Experimental and Computational Evidence for the Formation of Iminopersulfinic Acids
Clennan, Edward L.,Chen, Ming-Fang,Greer, Alexander,Jensen, Frank
, p. 3397 - 3402 (2007/10/03)
An experimental and computational study of the reactions of singlet oxygen with N-substituted sulfenamides is reported. Intermediates capable of epoxidizing norbornene were observed during the photooxidations of three sulfenamides. These results are used to argue for formation of iminopersulfinic acids. The structural integrity of two iminopersulfinic acids was supported by their successful location at the MP2/6-31G* level of theory. Furthermore, the inability to locate computationally significant persulfinimide precursors suggests that the iminopersulfinic acids form by enelike reactions involving near-simultaneous addition of singlet oxygen to sulfur and hydrogen abstraction.