32907-02-1Relevant academic research and scientific papers
Iodobenzene dichloride as a stoichiometric oxidant for the conversion of alcohols into carbonyl compounds; two facile methods for its preparation
Zhao, Xue-Fei,Zhang, Chi
, p. 551 - 557 (2007)
A highly efficient and mild procedure is described for the oxidation of different types of alcohols using 2,2,6,6-tetramethylpiperidin-1-yloxy (TEMPO) as the catalyst, iodobenzene dichloride (PhICl2) as a stoichiometric oxidant, and pyridine as the base. This procedure also smoothly oxidizes 1,2-diols to α-hydroxy ketones or α-diketones depending upon the amount of iodobenzene dichloride used. A competitive study shows that using the 2,2,6,6-tetramethylpiperidin-1-yloxy/iodobenzene dichloride/pyridine system aliphatic secondary alcohols are preferentially oxidized over aliphatic primary alcohols. In addition, two very convenient and high yielding procedures for the preparation of iodoarene dichlorides from iodoarenes have been developed. One employs solid sodium chlorite as a chlorinating agent in dilute hydrochloric acid solution; the other uses sodium hypochlorite as a chlorinating agent still in hydrochloric acid solution, which is more robust than the sodium chlorite system. Typically, the preparation of iodobenzene dichloride from iodobenzene was performed in five minutes using the sodium hypochlorite/hydrochloric acid system. Georg Thieme Verlag Stuttgart.
Willgerodt-Type Dichloro(aryl)-λ 3-Iodanes: A Structural Study
Daniliuc, Constantin G.,Gilmour, Ryan,Neufeld, Jessica,Sarie, Jér?me C.
, p. 4408 - 4416 (2019/11/21)
Crystallographic structural analysis of four electronically diverse Willgerodt-type reagents is disclosed together with a solution-phase NMR analysis. These data reveal a plethora of intermolecular non-covalent interactions and confirm the expected T-shape geometry of the reagents. In all cases the I-Cl bonds are orthogonal to the plane of the aryl ring. This study provides important structural insights into this venerable class of dichlorination reagent and has implications for crystal engineering.
Ceric ammonium nitrate as the novel oxidizing agent for the facile synthesis of (dichloroiodo)arenes
Tale, Nilesh P.,Shelke, Amol V.,Karade, Nandkishor N.
experimental part, p. 2959 - 2965 (2012/07/27)
Ceric ammonium nitrate (CAN) has been found to be a remarkable oxidizing agent for the oxidative conversion of iodoarenes to (dichloroiodo)arenes in acetic acid using aqueous HCl. The reaction of CAN with HCl generates in situ molecular chlorine, which is responsible for the oxidation. This method avoids the use of hazardous, toxic, and corrosive gaseous chlorine.
One-pot preparations of (dichloroiodo)arenes from some arenes
Lulinski, Piotr,Obeid, Nicolas,Skulski, Lech
, p. 2433 - 2434 (2007/10/03)
Arenes (ArH) were substituted with some transient I3+ species, generated in situ in appropriate, anhydrous I2/NaIO4 or NaIO3/AcOH/Ac2O/concd H2SO4 mixtures, to form soluble organ
Liquid-phase and biphasic chlorination of some iodoarenes to form (dichloroiodo)arenes with sodium peroxodisulfate as the oxidant
Baranowski,Plachta,Skulski,Klimaszewska
, p. 435 - 437 (2007/10/03)
Liquid-phase and biphasic (CCl4/concd hydrochloric acid) chlorination of some iodoarenes to form the corresponding (dichloroiodo)arenes, prepared in 60-100% crude yields, are reported; dichlorine is produced as follows: Na2S2OP8 + 2 HCl (conc. aq.) → Cl2 + 2 NaHSO4.
Biphasic chlorination of iodoarenes to (dichloroiodo)arenes
Krassowska-?wiebocka, Barbara,Prokopienko, Grazyna,Skulski, Lech
, p. 1409 - 1410 (2007/10/03)
A two-phase (CCl4/conc. hydrochloric acid) chlorination of some iodoarenes to the corresponding (dichloroiodo)arenes, prepared in 50-98% crude yields, is reported. Dichlorine is produced in the aqueous phase as follows: KClO3 (solid) + 6 HCl (conc. aq.) → ↑3Cl2 + KCl + 3H2O.
