233-64-7Relevant academic research and scientific papers
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.
On the Reactions of 2,3-Dichloro-1,4-Naphthoquinone and 5-Chloro-6H-6-Oxoanthra[1,9-cd]isoxazole with Ketoximes and 1,2-Naphthaquinone Dioxime
Timoshkova,Gornostaev
, p. 1486 - 1488 (2007/10/03)
In the reaction of 2,3-dichloro-1,4-naphthoquinone and 5-chloro-6H-6-oxoanthra[1,9-cd]-isoxazole with ketoximes one of chlorine atoms is replaced by the oxime residue. In the reaction of 2,3-dichloro-1,4-naphthoquinone with 1,2-naphthoquinone dioxime 1,2-
Alkylaminonitrobenzenes by Vicarious Nucleophilic Amination with 4-(Alkylamino)-1,2,4-triazoles
Katritzky, Alan R.,Laurenzo, Kathleen S.
, p. 3978 - 3982 (2007/10/02)
A series of 4-(alkylamino)-1,2,4-triazoles transfer the alkylamino group to the 4-position of nitrobenzene and various 3-substituted nitrobenzenes, with no detectable ortho substitution.By contrast 2-nitrothiophene reacts in the 3-position and 2-nitronaphthalene in the 1-position; 1-nitronaphthalene gives a mixture of products derived from dominant 2- with some 4-substitution.The orientations are discussed and rationalized.
