1074-11-9Relevant articles and documents
Copper-catalyzed regioselective chloroamination of alkenes with chlorotrimethylsilane and n-fluorobenzenesulfonimide under microwave-assisted conditions
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A copper-catalyzed chloroamination of alkenes with chlorotrimethylsilane and N-fluorobenzenesulfonimide has been developed. The reactions were complete within 1 h at 120 °C by means of microwave heating. The present chloroamination proceeds with a perfect regioselectivity and is compatible with various functional groups. The preliminary mechanistic investigation revealed that the reaction involves a radical process. The utility of the present method was demonstrated by scalable, operationally simple and safe system.
STRUCTURE OF POLYMERS ON THE BASIS OF CHLORINATED STYRENE AND SODIUM DISULPHIDE
Todorova, D.,Mladenov, Iv.,Marcov, M.
, p. 453 - 456 (1984)
A polycondensation of a mixture of halogen derivatives of styrene obtained at direct chlorination of styrene and containing ca. 80 percent α,β-dichloroethylbenzene and sodium disulphide was studied.Polysulphide liquid low molecular polymers were obtained.By means of molecular spectroscopy, fractionation and the elemental analysis the structure of the synthesized products was studied.It was proved, that the essential unit is the styrenedisulphide one.The role of monofunctional monomer and of nonchlorinated styrene in reaction conditions was indicated
Quaternary ammonium polychlorides as efficient reagents for chlorination of unsaturated compounds
Zelikman,Tyurin,Smirnov,Zyk
, p. 1541 - 1546 (1998)
Chlorination of unsaturated compounds by benzyltributylammonium polychlorides results in higher yields of addition products compared to those obtained with molecular chlorine.
Reaction of Styrene with Chlorine Dioxide
Loginova,Chukicheva, I. Yu.,Kuchin
, (2018)
Reaction of styrene with chlorine dioxide under various conditions selectively produces 1-phenyl- 2-chloroethanone, with 1-phenyl-2-chloroethanol, 2-hydroxy-1-phenylethanone, (1,2-dichloroethyl)benzene, (2-chloro-1-phenyl)ethene, and (1,2,2-trichloroethyl
Dichlorination of olefins with diphenyl sulfoxide/oxalyl chloride
Ding, Rui,Huang, Shuai,Wang, Qiyi,Liu, Yongguo,Sun, Baoguo,Tian, Hongyu
, p. 2319 - 2330 (2020)
The combination of diphenyl sulfoxide and oxalyl chloride was used to accomplish the dichlorination of olefins, in which chlorodiphenylsulfonium salt generated in situ was proposed to be the real active species as a chloronium ion source.
The Electrochemical cis-Chlorination of Alkenes
Strehl, Julia,Fastie, Cornelius,Hilt, Gerhard
supporting information, p. 17341 - 17345 (2021/10/23)
The first example for the electrochemical cis-dichlorination of alkenes is presented. The reaction can be performed with little experimental effort by using phenylselenyl chloride as catalyst and tetrabutylammoniumchloride as supporting electrolyte, which also acts as nucleophilic reagent for the SN2-type replacement of selenium versus chloride. Cyclic voltammetric measurements and control experiments revealed a dual role of phenylselenyl chloride in the reaction. Based on these results a reaction mechanism was postulated, where the key step of the process is the activation of a phenylselenyl chloride-alkene adduct by electrochemically generated phenylselenyl trichloride. Like this, different aliphatic and aromatic cyclic and acyclic alkenes were converted to the dichlorinated products. Thereby, throughout high diastereoselectivities were achieved for the cis-chlorinated compounds of >95 : 5 or higher.
Selective monochlorination of unsymmetrical vicinal diols with chlorinated iminium chlorides
Li, Chengyang,Li, Xiaotong,Wang, Yu,Wu, Xiaoyu,Xie, Xiaomin,Yang, Liqun,Zhang, Zhaoguo
, (2020/03/23)
Chlorinated iminium chlorides have been identified to promote the highly efficient and selective mono-chlorination of unsymmetrical vicinal diols. Vilsmeier reagent, namely, (chloromethylene)dimethyliminium chloride, enables highly reactive and regioselective chlorination of 1,2- and 1,3-diols featured one secondary benzylic hydroxy group and one primary aliphatic hydroxy group to give the corresponding 1,2- and 1,3-chlorohydrins. Viehe's salts (α,α-dichloro iminium salts) exhibit excellent reactivity and good selectivity for vicinal diols to give the corresponding chlorohydrin carbamates via a cyclic intermediate in situ. The chlorination protocols tolerate diverse functional groups, including halogens, naphthalene rings, nitro, and cyano. Moreover, the optical purity of chiral diols could be retained during this chlorination reaction.
