78488-98-9Relevant academic research and scientific papers
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. XIV. ARYLSULFONYLIMINATION OF N-ARYLSULFONYL-2,4-DINITROBENZENE- AND N-ARYLSULFONYL-2,4,6-TRINITROBENZENESULFENAMIDES
Koval', I.V.,Oleinik, T.G.,Kremlev, M.M.
, p. 483 - 487 (2007/10/02)
N-Alkyl-N-arylsulfonyl-2,4-dinitrobenzenesulfenamides are not iminated by N-sodio-N-chlorosulfonamides.This is due to the impossibility of the formation of the mesomeric anion of the N-arylsulfonyl-2,4-dinitrobenzenesulfenamide.N-Arylsulfonyl-2,4-dinitrobenzenesulfenamides are smoothly iminated by N-sodio-N-chlorosulfonamides in polar media with the formation of N,N'-bis(arylsulfonyl)-2,4-dinitrobenzenesulfinamidines.In spite of the high stability of the mesomeric anion of the N-arylsulfonyl-2,4,6-trinitrobenzenesulfenamide, it was not possible to realize its imination.This is clearly due to the steric factor or to the weak nucleophilicity of the iminated sulfur.
