75560-71-3Relevant academic research and scientific papers
Synthesis of Halogenated Anilines by Treatment of N, N-Dialkylaniline N-Oxides with Thionyl Halides
Reed, Hayley,Paul, Tyler R.,Chain, William J.
, p. 11359 - 11368 (2018/08/06)
The special reactivity of N,N-dialkylaniline N-oxides allows practical and convenient access to electron-rich aryl halides. A complementary pair of reaction protocols allow for the selective para-bromination or ortho-chlorination of N,N-dialkylanilines in up to 69% isolated yield. The generation of a diverse array of halogenated anilines is made possible by a temporary oxidation level increase of N,N-dialkylanilines to the corresponding N,N-dialkylaniline N-oxides and the excision of the resultant weak N-O bond via treatment with thionyl bromide or thionyl chloride at low temperature.
The Chlorination of Some N,N-Dimethylanilines with 1,3,5-Trichloro-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione (Trichloroisocyanuric Acid)
Rosevear, Judi,Wilshire, John F. K.
, p. 843 - 852 (2007/10/02)
The reaction of some representative N,N-dimethylanilines and of Fischer's base (1,3,3-trimethyl-2-methyleneindoline) with trichloroisocyanuric acid in concetrated sulfuric acid has been investigated.In many cases mixtures of chlorinated products were obtained; these mixtures were examined both by gas-liquid chromatography and by proton magnetic resonance spectroscopy.The reaction of N,N-dimethylaniline with dichloroisocyanuric acid was also studied.A feature of these chlorinations is the marked tendency for substitution to occur ortho to the dimethylamino group.This behaviour therefore differs from that reported for the corresponding brominations involving dibromoisocyanuric acid, where meta-substitution was observed.
