599-71-3Relevant articles and documents
Selective trapping of SNO-BSA and GSNO by benzenesulfinic acid sodium salt: Mechanistic study of thiosulfonate formation and feasibility as a protein S-nitrosothiol detection strategy
Reeves, Benjamin D.,Hilmer, Jonathan K.,Mellmann, Lisa,Hartzheim, Myra,Poffenberger, Kevin,Johnson, Keith,Joshi, Neelambari,Singel, David J.,Grieco, Paul A.
, p. 5707 - 5710 (2013)
The conversion of S-nitrosothiols to thiosulfonates by reaction with the sodium salt of benzenesulfinic acid (PhSO2Na) has been examined in detail with the exemplary substrates S-nitrosoglutathione (GSNO) and S-nitrosylated bovine serum albumin (SNO-BSA). The reaction stoichiometry (2:1, PhSO2Na:RSNO) and the rate law (first order in both PhSO 2Na and RSNO) have been determined under mild acidic conditions (pH 4.0). The products have been identified as the corresponding thiosulfonates (GSSO2Ph and BSA-SSO2Ph) along with PhSO2NHOH obtained in a 1:1 ratio. GSH, GSSG, and BSA were unreactive to PhSO 2Na.
Nondirected, cu-catalyzed sp3 C-H aminations with hydroxylamine-based amination reagents: Catalytic and mechanistic studies
Wang, Anqi,Venditto, Nicholas J.,Darcy, Julia W.,Emmert, Marion H.
supporting information, p. 1259 - 1268 (2017/05/29)
This work demonstrates the use of hydroxylamine-based amination reagents RSO2NH-OAc for the nondirected, Cu-catalyzed amination of benzylic C-H bonds. The amination reagents can be prepared on a gram scale, are benchtop stable, and provide benzylic C-H amination products with up to 86% yield. Mechanistic studies of the established reactivity with toluene as substrate reveal a ligand-promoted, Cu-catalyzed mechanism proceeding through Ph-CH2(NTsOAc) as a major intermediate. Stoichiometric reactivity of Ph-CH2(NTsOAc) to produce Ph-CH2-NHTs suggests a two-cycle, radical pathway for C-H amination, in which the decomposition of the employed diimine ligands plays an important role.
REACTION OF HYDROXYLAMINE WITH BENZENESULFONYL CHLORIDE. X-RAY CRYSTAL STRUCTURE OF PILOTY'S ACID AND OTHER BENZENESULFONYLHYDROXYLAMINES.
Scholz, John N.,Engel, Paul S.,Glidewell, Christopher,Whitmire, Kenton H.
, p. 7695 - 7708 (2007/10/02)
The X-ray crystal structures of the four stable phenylhydroxylamines (PhSO2NHOH, (PhSO2)2NOH, PhSO2NHOSO2Ph, (PhSO2)2NOSO2Ph), and of PhSO3-+H3NHNSO2Ph are presented.The last of these is a by-product obtained during the isolation of PhSO2NHOH (Piloty's Acid).The formation of and the bonding in these molecules are discussed.