33427-17-7Relevant articles and documents
Gas-Phase Atomic Halogenation Reactions Using Iodine Monochloride
Tanner, Dennis D.,Rowe, Jeffrey E.,Potter, Alan
, p. 457 - 460 (1986)
The mechanism of the photoinitiated gas-phase halogenation reactions of alkanes using iodine monochloride has been reported previously as proceeding via a radical chain process to form the corresponding alkyl chlorides.This is in marked contrast to analogous reactions with bromine-chlorine mixtures, thought to form bromine chloride, which produce alkyl bromides via a radical process.An attempt has been made to rationalize this anomaly.In this paper evidence is offered to demonstrate that under photolytic conditions, alkanes and iodine monochloride react via a radical chain process to produce initially the corresponding alkyl iodide.The reaction is shown to proceed by a chain process where the chain-carrying species is the chlorine atom.However, the reaction is complicated by further ionic reactions of the alkyl iodides, whith iodine monochloride, which produce alkyl chlorides and other polyhalogenated materials.
New electrophilic iodochlorinating systems based on iodine(+1)
Zyk,Sereda,Sosonyuk,Zefirov
, p. 843 - 844 (1997)
Two new convenient systems for electrophilic iodochlorination of olefins are proposed: KIO3 + I2 + HCl (in aqueous solutions) and KICl4 + I2 (in organic solvents).
PYRIDINIUM DICHROMATE IN ORGANIC SYNTHESIS: A CONVENIENT OXIDATION OF OLEFIN-IODINE COMPLEXES TO α-IODO KETONES
D'Ascoli, R.,D'Auria, M.,Nucciarelli, L.,Piancatelli, G.,Scettri, A.
, p. 4521 - 4522 (1980)
Cyclic α-iodo ketones are obtained directly by oxidation of olefin-iodine complexes with pyridinium dichromate.
Selective conversion of epoxides to vic-halo alcohols and symmetrical or unsymmetrical dihalides by triphenylphosphine/2,3-dichloro-5,6-dicyano-1,4- benzoquinone (DDQ) in the presence of quaternary ammonium halides
Iranpoor, Nasser,Firouzabadi, Habib,Aghapour, Ghasem,Nahid, Azarmidokht
, p. 1885 - 1891 (2007/10/03)
A new method is described for the efficient and selective conversion of epoxides to vic-halo alcohols or symmetrical and unsymmetrical dihalides using PPh3/DDQ/R4NX (X = Cl, Br, I) as a mixed-reagent system.
Carbon-halogen bond activation by Nickel catalyst: Synthesis of alkenes, from 1,2-dihalides
Malanga, Corrado,Mannucci, Serena,Lardicci, Luciano
, p. 1021 - 1028 (2007/10/03)
Unsaturated hydrocarbons can easily be prepared in a few seconds starting from 1,2 dibromides in the presence of a catalytic amount of Nickel diphenylphosphinoethane dichloride (NidppeCl2) and tri.n.butyl tin hydride, (TBTH) at room temperature. The dependencie of the nature of starting dihalides is investigated.
Versatile iodination of olefins by potassium dichloroiodate(I)
Zefirov,Sereda,Sosonuk,Zyk,Likhomanova
, p. 1359 - 1361 (2007/10/02)
The versatile electrophilic iodination of double bonds with potassium dichloroiodate(I) is described. In most examples various β-substituted iodides, particularly vic-iodochlorides were synthesised in excellent yields.
Halogenation using quaternary ammonium polyhalides XXVII.1 chloroiodination of alkenes with benzyltrimethyl-ammonium dichloroiodate
Kajigaeshi, Shoji,Moriwaki, Masayuki,Fujisaki, Shizuo,Kakinami, Takaaki,Okamoto, Tsuyoshi
, p. 3033 - 3035 (2007/10/02)
The reaction of alkenes with benzyltrimethylammonium dichloroiodate in dichloromethane gave the chloro iodo adducts in anti-stereospecific and regioselective manner; in methanol these adducts were obtained along with methanol-incorporated products.
An Efficient Method for the Copper(II)-promoted Stereoselective Iodofunctionalization of Alkenes
Barluenga, Jose,Rodriguez, Miguel A.,Campos, Pedro J.
, p. 2807 - 2809 (2007/10/02)
A mixture of iodine and CuO*HBF4 reacts stereoselectively with alkenes in the presence of a wide variety of nucleophiles (water, MeOH, HCO2H, AcOH, EtCOOH, NaNO2, KSCN, NaSO2Ar, LiCl, LiBr, NaI, Et3SiH, and MeOPh) to give the corresponding 2-functionalized iodo compounds.A regio chemistry study is also reported.
Iodine Cyanide Promoted Iodination of Aromatic Compounds. A Simple Synthesis of 1-Iodopyrene
Radner, Finn
, p. 481 - 484 (2007/10/02)
A simple method for the iodination of reactive aromatic compounds, using ICN in the presence of a Lewis acid as the source of iodine, is presented. 1-Iodopyrene is obtained in 81percent isolated yield from the reaction of pyrene and ICN with AlCl3 in CH3NO2/(C2H5)2O.Anthracene undergoes partial chlorination in the presence of AlCl3, but with BF3, 9-iodoanthracene is obtained in 48percent isolated yield.
BROMO- AND IODOFUNCTIONALIZATION OF OLEFINS BY MEANS OF THE MERCURY(II) SALT-HALOGEN COMBINATION
Barluenga, Jose,Martinez-Gallo, Jose M.,Najera, Carmen,Yus, Miguel
, p. 2416 - 2443 (2007/10/02)
Mercury(II) salts (fluoride, chloride, bromide, formate, acetate, trifluoroacetate, propionate, benzoate, nitrate, methanesulphonate, toluene-p-sulphonate, thiocyanate, and toluene-p-sulphinate) reacted with monoolefines and bromine or iodine to give 1,2-bifunctionalized products resulting from the addition of the halogen and the mercury(II) salt anion selectively.The addition was regiospecific for styrene and for 3,3-dimethylbut-1-ene affording Markownikoff type products, respectively.In the case of hex-1-ene both regioisomers were obtained.For cyclic alkenes trans-1,2-derivatives were stereoselectively obtained.Cycloocta-1,5-diene gave the monoaddition products.Buta-1,3-diene underwent mainly 1,2-addition and allylic derivatives gave the corresponding 1,2,3-trifunctionalized compounds.A possible ionic mechanism is proposed to explain the obtained addition products.
