18112-84-0Relevant academic research and scientific papers
IMINATION OF SULFUR-CONTAINING COMPOUNDS. XXIV. EFFECT OF THE ACIDIC CHARACTERISTICS OF THIOLS ON THE IMINATION OF SODIUM THIOLATES BY DICHLOROSULFONAMIDES
Koval', I. V.,Tarasenko, A. I.,Kremlev, M. M.
, p. 362 - 367 (2007/10/02)
The ability of sodium thiolates to be iminated by dichlorosulfonamides is due to a series of factors and primarily to the acidic characteristics of the initial thiols.The sodium salts of thiols with pKa > 8 are iminated comparatively readily by dichlorosulfonamides.Decrease in the pKa values of the thiols to 5-7 leads to a decrease in the imination rate and in the yields of the respective N,N'-bis(arylsulfonyl)sulfinamidines.The sodium salts of thiols with pKa 5 are not iminated by dichlorosulfonamides.Investigation of the acidic characteristics of the N,N'-bis(arylsulfonyl)sulfinamidines showed that substituents in the sulfinamidine fragment of the molecule make a larger contribution to the change in the acidic characteristics of the compounds than substituents in the arenesulfonyl fragment.
IMINATION OF SULFUR-CONTAINING COMPOUNDS. XXV. ARYLSULFONYLIMINATION OF BIS(ARYLSULFENYL)AMINES
Koval', I. V.,Tarasenko, A. I.,Kremlev, M. M.,Naumenko, R. P.
, p. 1060 - 1064 (2007/10/02)
The imination of bis(arylsulfenyl)amines with N-sodio-N-chlorosulfonamides takes place anomalously with the formation of N,N'-bis(arylsulfonyl)arenesulfinamidines and N-(arylsulfonyl)arenesulfinamidines.This is due to the instability of the sulfur-nitroge
IMINATION OF SULFUR-CONTAINING COMPOUNDS. XXIII. EFFECT OF THE ACIDIC CHARACTERISTICS OF N-SUBSTITUTED SULFENAMIDES ON THEIR ABILITY TO BE IMINATED BY THE SODIOCHLOROAMIDES OF SULFONIC ACIDS
Koval', I. V.,Oleinik, T. G.,Tarasenko, A. I.,Kremlev, M. M.
, p. 2358 - 2365 (2007/10/02)
The ability of N-substituted sulfenamides to be iminated by the sodiochloroamides of sulfonic acids is due primarily to their acidity and to the type of solvent employed.N-Substituted sulfonamides with pKa > 11.0 are imidated by the sodiochloroamides of sulfonic acids in acetone.The imination of N-substituted sulfenamides with pKa 8-11 must be carried out in strongly basic solvents with high dielectric constants (an aqueous alkaline medium, pyridine, etc.); sulfenamides with pKa 8 are iminated by the sodiochloroamides of sulfonic acids in the form of the sulfenamide anion.
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.
