5877-96-3Relevant articles and documents
Rh/Wudaphos-Catalyzed Asymmetric Hydrogenation of Sodium α-Arylethenylsulfonates: A Method to Access Chiral α-Arylethylsulfonic Acids
Yin, Xuguang,Chen, Caiyou,Dong, Xiu-Qin,Zhang, Xumu
, p. 2678 - 2681 (2017)
A highly enantioselective hydrogenation of various sodium α-arylethenylsulfonates catalyzed by Rh/chiral ferrocenyl bisphosphorus ligand (Wudaphos) was successfully developed to construct a series of chiral α-arylethylsulfonic acids in the presence of CF3SO3H with full conversion and good to excellent enantioselectivity (>99% conversion, up to 96% ee) under mild reaction conditions for the first time. Moreover, the control experiment results showed that the non-covalent ion pair interaction between the α-arylethenylsulfonic acid and the Wudaphos ligand plays an important role in this asymmetric hydrogenation system.
Competing sulfonylation and phosphonylation following rearrangement of an O-sulfonyl-N-phosphinoylhydroxylamine with tert-butylamine: Demonstration of a phosphonamidic-sulfonic anhydride intermediate and 18O-labelling evidence on how it may be formed
Harger, Martin J.P.
, p. 3390 - 3395 (2007/10/03)
Reaction of R(Ph)P(O)NHOSO2Bn (R = PhMeCH) with Bu tNH2 in CH2Cl2 gives a mixture of RP(O)(NHPh)NHBut and ButNHSO2Bn, the proportion of the sulfonamide increasing steadily (14.6% to 32.9%) as the concentration of amine is reduced (8.0 to 0.2 mol dm-3). Apparently the phenyl and sulfonate groups in the substrate become transposed, giving a phosphonamidic-sulfonic anhydride RP(O)(NHPh)OSO2Bn which then reacts at the phosphorus or sulfur atom to give the final products; an authentic sample of the anhydride gives similar mixtures of products. Substrate labelled with 18O in the sulfonyl position (57 mol% one 18O atom) gives sulfonamide containing most but not all of the label (43.7 mol% one 18O atom with 2.0 mol dm-3 amine). This implies partial equilibration of the three sulfonate oxygen atoms during rearrangement, or after the anhydride intermediate has been formed.
A CAUTIONARY COMMENT ON A RECENT COMMUNICATION ENTITLED "A MEASURE OF CHARGE TRANSFER (ρ) VERSUS A MEASURE OF BOND TIGHTNESS (ρij) IN THE TRANSITION STATE"
King, J. F.,Skonieczny, S.
, p. 5001 - 5004 (2007/10/02)
We present evidence that the reaction of anilines with ArCH2SO2Cl and ArCH2SO2F goes mainly via the sulfene (ArCH=SO2) and is not a simple nucleophilic displacement at sulfur, as was assumed in the above paper by I.Lee and H.K.Kang (Tetrahedron Lett. 28, 1183 (1987)), and hence that their conclusions about the interpretation of ρ and ρXY values are unfounded.