32704-10-2Relevant academic research and scientific papers
A Novel Aromatic Iodination Method Using F2
Rozen, Shlomo,Zamir, Dov
, p. 3552 - 3555 (2007/10/02)
A new method for direct aromatic iodination with IF, made in situ from the corresponding elements, is described.Depending on the reaction time and temperature, mono- or polyiodination can be achieved.Even deactivated aromatic rings can be directly iodinated without the presence of any Friedel-Crafts catalyst.Sensitive groups such as aromatic aldehydes are not affected by the reagent.
STOICHIOMETRIC AND CATALYTIC OXIDATIVE IODINATION OF AROMATIC COMPOUNDS IN THE PRESENCE OF NITROGEN-CONTAINING OXIDIZING AGENTS IN AQUEOUS TRIFLUOROACETIC ACID
Makhon'kov, D. I.,Cheprakov, A. V.,Beletskaya, I. P.
, p. 2029 - 2035 (2007/10/02)
The conditions for oxidative monoiodination of benzene, halogenobenzenes, toluene, halogenotoluenes, and p-toluic acid in solvents based on trifluoroacetic acid were studied.Yields of the respective iodoarenes close to quantitative were obtained in systems containing 10-20 vol. percent of water in the solvent with equimolar amounts of alkali-metal metal iodides in relation to the substrate in the presence of stoichiometric (under anaerobic conditions) or catalytic (in the presence of oxygen or air) amounts of alkali-metal nitrates.The analogous reactions with nitrites can only be conducted under aerobic conditions.These iodinating systems are compared with systems based on acetic acid containing iodine and mixtures of sulfuric and nitric acids.The conditions for the iodination of toluene and for the transformations of the obtained iodotoluenes in the presence of nitrogen-containing oxidizing agents in trifluoroacetic acid solutions were studied in detail.It was shown that p-iodotoluene undergoes ipso-nitrodeiodination to a significant degree under these conditions.It is supposed that the iodinating agent in the investigated systems is trifluoroacetyl hypoiodite.Data on the assignment of the PMR spectra of the synthesized isomeric nitroiodotoluenes and chloroiodotoluenes by a simple additive method are given.
Direct Aromatic Periodination
Mattern, Daniell Lewis
, p. 3051 - 3053 (2007/10/02)
Periodic acid and iodine in concentrated sulfuric acid exhaustively iodinated unactivated aromatic substrates.Thus benzene, nitrobenzene, benzoic acid, chlorobenzene, phthalic anhydride, and toluene were all converted to their periodo derivatives.Benzonitrile was converted to pentaiodobenzamide.This direct method compared favorably with the only general periodination procedure available, a mercuration/iododemercuration sequence.Partially iodinated products were obtained under less vigorous conditions.Thus, triiodo derivatives were obtained from nitrobenzene, benzo-ic acid, and toluene; tetraiodo derivatives were obtained from benzene, chlorobenzene, and trifluorobenzene.
