22900-27-2Relevant academic research and scientific papers
Enantiomeric separation of sulfonium ions by capillary electrophoresis using neutral and charged cyclodextrins
Valenzuela, Francisco A.,Green, Thomas K.,Dahl, Darwin B.
, p. 3612 - 3618 (1998)
Capillary zone electrophoresis was successfully applied, for the first time, to the chiral separation of structurally related sulfonium ions, using sodium phosphate buffer pH 2.5 withy β-cyclodextrin (β-CD) or sutfated-β-cyclodextrin (S-β-CD) as the chira
MECHANISM OF ONE-ELECTRON ELECTROCHEMICAL REDUCTIVE CLEAVAGE REACTIONS OF SULFONIUM SALTS.
Saeva,Morgan
, p. 4121 - 4125 (2007/10/02)
Irreversible one-electron reduction potentials (E//p) were measured for 12 arylmethyl(substituted-alkyl)sulfonium salts (aryl equals phenyl and 1-naphthyl). One-electron reduction produced homolytic sulfur-carbon sigma -bond cleavage in each of the sulfon
One-Electron Chemical Reductions of Phenylalkylsulfonium Salts
Beak, Peter,Sullivan, Thomas A.
, p. 4450 - 4457 (2007/10/02)
Twenty-two arylalkylsulfonium salts have been reduced with potassium in graphite in tetrahydrofuran and the sulfide products identified.Two trialkylsulfonium salts did not reduce under these conditions.Comparison of the sulfides from a series of monophenylalkylsulfonium salts reveals a leaving-group propensity of benzyl > secondary > primary > methyl > phenyl in a ratio of 28:(6.0 +/- 0.3):1.0:(0.53 +/- 0.09): 0.05.The cleavage ratio is shown to be independent of the electron source and the homogeneity of heterogeneity of the reaction in two cases.Multiplicative transitivity of the above ratios is not observed, although the same qualitative order is found for other comparisons.These results are interpreted in terms of the initial formation of a ?-ligand radical anion sulfonium cation, which undergoes cleavage to a carbon radical and a sulfide.This appears to be the first evidence for this type of structure in a sulfur system.Leaving-group propensities different from the above order are observed in reductions of diphenylsulfonium and benzo-fused sulfonium salts, and rationales are offered.The intermediates in these reactions appear to be different from those involved in radical additions to, or displacements on, sulfur.
