5350-56-1Relevant articles and documents
Direct amination of 1-substituted 3,5-dinitrobenzenes by 1,1,1-trimethylhydrazinium iodide
Rozhkov, Vladimir V.,Shevelev, Svyatoslav A.,Chervin, Ivan I.,Mitchell, Alexander R.,Schmidt, Robert D.
, p. 2498 - 2501 (2007/10/03)
The amination of 1-X-3,5-dinitrobenzenes via the vicarious nucleophilic substitution of hydrogen (VNS) with 1,1,1-trimethylhydrazinium iodide (TMHI) in the presence of t-BuOK or NaOMe in DMSO was studied. It was observed (when X = OMe, OCH2CF3, OCH2CF2CF2H, OPh) that the amination occurs regioselectively (ratio of ortho/para-isomers is ~9:1) and with high yield. For X = SPh or SCH2Ph, the reaction proceeded with a low yield (less than 20%), with a ratio of ortho/para-isomers ≈1:1. For X = PhSO2 and 2 equiv of TMHI, a double amination occurs and 2,4-diamino-3,5- dinitro-1-phenylsulfonylbenzene predominates in the mixture of isomers. Under the same conditions, 1,3,5-trinitrobenzene undergoes a double amination to yield 2,4-diamino-1,3,5-trinitrobenzene. A proposed mechanism for this reaction is discussed.
Oxidation of Aryldialkylamines with Cerium(IV) Ammonium Nitrate and Thallium(III) Nitrate
Galliani, Guido,Rindone, Bruno
, p. 828 - 832 (2007/10/02)
Nine alkylmethylanilines were oxidised with cerium(IV)ammonium nitrate and thallium(III) nitrate in acetic acid, acetonitrile, and methanol.Reaction products were those deriving from demethylation, dealkylation, and aromatic nitration at positions ortho and para to the amino-group.The ratio between demethylation and dealkylation and between them and aromatic nitration is discussed in terms of (i) the oxidising power and electrophilicity of the reagent and (ii) the co-ordinative properties of the solvent.