ANODIC CHLORINATION OF SUBSTITUTED BENZENES - CHOICE OF THE CHLORINATION REAGENTS

被引:25
作者
GOURCY, J [1 ]
SIMONET, J [1 ]
JACCAUD, M [1 ]
机构
[1] PROD CHIM UGINE KUHLMANN,CTR RECH LYON,F-69310 PIERRE BENITE,FRANCE
关键词
D O I
10.1016/0013-4686(79)87103-0
中图分类号
O646 [电化学、电解、磁化学];
学科分类号
081704 ;
摘要
Some substituted benzenes ArH were anodically chlorinated in acetonitrile LiClO4 on a platinum electrode in the presence of either Cl- anion or a chlorinated Lewis acid (such as AlCl3). The overvoltage on the oxidation of Cl- caused by a strong complexation by some Lewis acid allows consideration that the anodic reaction passes through the radical cation of the aromatic substrate. In such conditions, polychlorinations are possible and in the specific case of toluene, it is shown that the reaction favors the parachlorotoluene formation. The influence of different parameters (for example, the ratio of the concentrations AlCl3/ArH, the nature of the Lewis acid) in such a reaction are discussed. © 1979.
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收藏
页码:1039 / 1046
页数:8
相关论文
共 19 条
[1]   ACIDITY IN NITROMETHANE .3. ELECTROCHEMICAL DETERMINATION OF NITROMETHANE BASICITY - DN/EO(H+S/H2) [J].
BAUER, D ;
FOUCAULT, A .
JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1976, 67 (01) :19-32
[2]  
BIONDA G, 1951, ANN CHIM-ROME, V41, P814
[3]  
BROCKMAN CJ, 1928, ELECTROORGANIC CHEM
[4]   Studies in chlorination II. The action of chlorine on boiling toluene. Preliminary notice [J].
Cohen, JB ;
Dawson, HM ;
Crosland, PF .
JOURNAL OF THE CHEMICAL SOCIETY, 1905, 87 :1034-1037
[5]  
FICHER F, 1916, CHEM BER, V49, P2473
[6]  
GHOSH JC, 1952, J SCI IND RES B, V11, P361
[7]  
GOUGHLIN P, 1902, AM CHEM J, V27, P63
[8]  
Jayles P, 1929, CR HEBD ACAD SCI, V189, P686
[9]  
Jeunehomme W, 1934, CR HEBD ACAD SCI, V199, P1027
[10]   COORDINATION DISPROPORTIONATION EQUILIBRIA IN SOLUTION .I. ALUMINUM CHLORIDE IN ACETONITRILE [J].
LIBUS, W ;
PUCHALSK.D .
JOURNAL OF PHYSICAL CHEMISTRY, 1967, 71 (11) :3549-&