35113-90-7Relevant academic research and scientific papers
An efficient chlorination of aromatic compounds using a catalytic amount of iodobenzene
Li, Ting-Ting,Xu, Cui,Xiang, Chang-Bin,Yan, Jie
, p. 535 - 538 (2013/07/27)
An efficient method was developed for chlorination of aromatic compounds with electron-donating groups using iodobenzene as the catalyst and m-chloroperbenzoic acid as the terminal oxidant in the presence of 4-methylbenzenesulfonic acid in THF at room temperature for 24 h, and a series of the monochlorinated compounds was obtained in good yields. In this protocol, the catalyst iodobenzene was first oxidized into the hypervalent iodine intermediate, which then treated with lithium chloride and finally reacted with aromatic compounds to form the chlorinated compounds.
Highly Selective Aromatic Chlorinations. Part 2. The Chlorination of Substituted Phenols, Anisoles, Anilines, and Related Compounds with N-Chloroamines in Acidic Solution
Smith, John R. Lindsay,McKeer, Linda C.,Taylor, Jonathan M.
, p. 385 - 392 (2007/10/02)
Phenols, anisoles, anilines, and related compounds are chlorinated in trifluoroacetic acid at room temperature by N-chlorodialkylamines and N-chlorotrialkylammonium salts.With monsubstituted compounds and their 2- and 3-substituted derivatives the reaction occurs efficiently and selectively at the 4-position.The reactivity of these substrates and the selectivity of their chlorinations are determined by electronic rather than steric effects of the substituent.Blocking the reaction with a substituent at the 4-position generally leads to only poor or moderate yields of the 2-chlorinated product.Evidence for radical and cation radical intermediates has been obtained in the reactions of some of the 4-substituted reactants and the mechanism of chlorination is discussed in the light of these findings.The reactions of selected substrates have been scaled up to give laboratory syntheses.
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.
