19985-30-9Relevant academic research and scientific papers
Kinetic study of the reactions of some 5-nitro-2-(4-nitrophenoxy)-3-x-thiophenes with aniline and 4-methoxyaniline in methanol
Frenna, Vincenzo,Macaluso, Gabriella,Consiglio, Giovanni,Guernelli, Susanna,Spinelli, Domenico
, p. 1877 - 1892 (2007/10/03)
The rate constants of the title reactions have been measured at various amine concentrations. The second-order kinetic constant for the amino substitution increases in a hyperbolic way as a function of the nucleophile concentration. The k3Am/k-1 ratio for each catalysed system is not a monotonic function of the X substituent. This result has been rationalized in the framework of the SB-GA (Specific Base-General Acid) mechanism of base catalysis.
Nitroarylamines via the Vicarious Nucleophilic Substitution of Hydrogen: Amination, Alkylamination, and Arylamination of Nitroarenes with Sulfenamides
Makosza, Mieczyslaw,Bialecki, Maciej
, p. 4878 - 4888 (2007/10/03)
A new reaction of sulfenamides with electrophilic arenes under basic conditions is described. The σ adducts formed from nitroarenes and the anions of sulfenamides undergo elimination of thiol to produce the corresponding o- and/or p-nitroanilines. This reaction is analogous to the known alkylation and hydroxylation of nitroarenes via the vicarious nucleophilic substitution of hydrogen (VNS). The reaction gives access to a wide range of substituted nitroanilines, nitronaphthylamines, and aminoheterocycles. By means of the reaction with N-alkyl- and N-arylsulfenamides, it is possible to obtain N-alkylnitroanilines and nitrodiarylamines. By varying the structure of sulfenamide and the reaction conditions, particularly the nature and concentration of the base, it is possible to control the orientation of animation.
Process for the preparation of aromatic amines
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, (2008/06/13)
Electrophilic aromatic compounds can be reacted with sulphenamides in the presence of bases to form the corresponding aromatic amines.
