23847-33-8Relevant articles and documents
A convenient method for the preparation of functionalized N-acylsulfenamides from primary amides
Musiejuk, Mateusz,Witt, Dariusz
supporting information, p. 305 - 310 (2016/02/18)
We have developed a convenient method for the synthesis of functionalized N-acylsulfenamides under mild conditions and in moderate to good yields. The designed method is based on the reaction of (5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)-disulfanyl derivatives with nitrogen nucleophiles generated from primary amides or imides and sodium hydride. The developed method allows for the preparation of N-acylsulfenamides bearing additional hydroxyl, carboxyl, or amino functionalities.
Pd(II)-catalyzed selective sulfenylation of arene C-H bonds using N-arylthiobenzamides as thiolation reagent and oxidant
Zhang, Xing-Song,Li, Guoxing,Zhang, Xing-Guo,Zhang, Xiao-Hong
, p. 5458 - 5464 (2015/08/03)
The palladium-catalyzed direct sulfenylation of arenes with N-arylthiobenzamides was developed for the synthesis of aryl sulfides. Additional oxidant was not required for the catalytic cycle because N-arylthiobenzamide was used as both thiolation reagent and oxidant. The selective mono- or di-sulfenylation could be controlled by addition of the amount of N-arylthiobenzamide. Excellent functional group tolerance was observed and thioethers or dithioethers were obtained in good yields.
IMINATION OF SULFUR-CONTAINING COMPOUNDS. XII. ARYLSULFONYLIMINATION OF N-ACYLARENESULFENAMIDES
Koval', I. V.,Oleinik, T. G.,Kremlev, M. M.
, p. 553 - 555 (2007/10/02)
Arylsulfonylimination at the sulfur of N-acylarenesulfenamides was realized for the first time with the sodiochloroamides of sulfonic acids, where the acyl represents aroyl and alkanoyl groups.The imination of N-acyl-p-nitrobenzenesulfenamides occurs in an aqueous alkaline medium, and this is evidently due to an increase in the nucleophilicity of the sulfur in the corresponding anion on account of the displacement of electronic charge toward it from the nitrogen atom.During the imination of N-acyl-p- and N-acyl-o-nitrobenzenesulfenamides in pyridine cleavage of the sulfur-nitrogen bond occurs, and the NO2C6H4S residue is iminated to form N,N'-bis(arylsulfonyl)-p- and N,N'-bis(arylsulfonyl)-o-nitrobenzenesulfinamidines.