Photochemical conversion of 4-chloroaniline into 4-alkylanilines

被引:15
作者
Coppo, P [1 ]
Fagnoni, M [1 ]
Albini, A [1 ]
机构
[1] Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
关键词
alkylation; photochemistry; alkyl halides; fragmentation reaction;
D O I
10.1016/S0040-4039(01)00709-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Irradiation of 4-chloroanilines in the presence of alkenes gives 4-(2′-chloroalkyl)-anilines. When the irradiation is carried out in the presence of NaBH4, 4-alkylanilines are obtained directly. The reaction appears to occur via the corresponding phenyl cation. © 2001 Elsevier Science Ltd.
引用
收藏
页码:4271 / 4273
页数:3
相关论文
共 9 条
[1]  
BAARDMAN F, 1983, Patent No. 79083
[2]   Smooth synthesis of aryl- and alkylanilines by photoheterolysis of haloanilines in the presence of aromatics and alkenes [J].
Fagnoni, M ;
Mella, M ;
Albini, A .
ORGANIC LETTERS, 1999, 1 (08) :1299-1301
[3]   META FUNCTIONALIZATION OF ANILINES AND PHENOL [J].
FUKUI, M ;
IKEDA, T ;
OISHI, T .
TETRAHEDRON LETTERS, 1982, 23 (15) :1605-1608
[4]   SPECIFIC ORTHO ALKYLATION OF AROMATIC-AMINES [J].
GASSMAN, PG ;
GRUETZMACHER, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :588-589
[5]   FORMATION AND REACTIVITY OF 4-OXOCYCLOHEXA-2,5-DIENYLIDENE IN THE PHOTOLYSIS OF 4-CHLOROPHENOL IN AQUEOUS-SOLUTION AT AMBIENT-TEMPERATURE [J].
GRABNER, G ;
RICHARD, C ;
KOHLER, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (25) :11470-11480
[6]   SYNTHESIS AND EVALUATION OF 4-ALKYLANILINES AS MAMMARY-TUMOR INHIBITING AROMATASE INHIBITORS [J].
HARTMANN, RW ;
BATZL, C .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1992, 27 (05) :537-544
[7]  
ROSSI RA, 1972, J AM CHEM SOC, V94, P783
[8]  
SAKAMOTO T, 1986, HETEROCYCLES, V24, P31
[9]  
SCHROETER R, 1957, HOUBENWEYL METHODEN, V11, P341