Synthesis of 1,3,5-tris[4-(diarylamino)phenyl]benzene and 1,3,5-tris(diarylamino)benzene derivatives

被引:47
作者
Plater, MJ [1 ]
McKay, M [1 ]
Jackson, T [1 ]
机构
[1] Univ Aberdeen, Dept Chem, Aberdeen AB24 3UE, Scotland
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 16期
关键词
D O I
10.1039/b002928i
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The title compounds were prepared by the copper catalysed Ullmann coupling of aromatic amines with aromatic aryl iodides. Full spectroscopic details are reported. Solutions of 1,3,5-tris(diarylamino)benzene derivatives in deuterated chloroform undergo hydrogen-deuterium exchange on the central ring and readily turn green owing to partial oxidation by traces of dissolved oxygen. The green colour is quenched by the addition of ascorbic acid. The solutions are more stable in chloroform that has been filtered through basic alumina to remove traces of acid. N-Arylbenzenesulfonamides can be converted to diarylamines by treatment with the sodium salt of an aniline.
引用
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页码:2695 / 2701
页数:7
相关论文
共 48 条
[1]  
BRANTLY TB, Patent No. 3719480
[2]  
BUSHBY RJ, 1996, J CHEM SOC CHEM COMM, P659
[3]   THE SCOPE OF THE KNOEVENAGEL SYNTHESIS OF AROMATIC SECONDARY AMINES [J].
BUUHOI, NP .
JOURNAL OF THE CHEMICAL SOCIETY, 1952, (NOV) :4346-4349
[4]   REARRANGED PRODUCTS FROM REACTION OF BENZENESULFONIC ACIDS WITH CAUSTIC [J].
BUZBEE, LR .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (10) :3289-&
[5]   ELECTROCHEMICAL AND SPECTROSCOPIC STUDIES OF CATION RADICALS .1. COUPLING RATES OF 4-SUBSTITUTED TRIPHENYLAMINIUM IONS [J].
CREASON, SC ;
WHEELER, J ;
NELSON, RF .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (26) :4440-4446
[6]  
Crofts P. C., 1988, J CHEM RES MINIPRINT, P2313
[7]  
ELMSORY SS, 1991, TETRAHEDRON LETT, V32, P4175
[8]   SYNTHESIS OF TERTIARY PHOSPHINE DERIVATIVES OF DIHYDROPHENOPHOSPHAZINE [J].
FREEMAN, HS ;
FREEDMAN, LD .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (26) :5373-5376
[9]   ACETYLDIARYLAMINES BY ARYLATION OF ACETANILIDES - SOME APPLICATIONS AND LIMITATIONS [J].
FREEMAN, HS ;
BUTLER, JR ;
FREEDMAN, LD .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (26) :4975-4978
[10]   Concerning triphenylamine-carbonic acid. [Preliminary announcement.] [J].
Goldberg, I ;
Nimerovsky, M .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1907, 40 :2448-2452