AlCl3-mediated migration of the benzamido group of N-phenoxybenzamide derivatives to the phenyl group

被引:12
作者
Miyazawa, E [1 ]
Sakamoto, T [1 ]
Kikugawa, Y [1 ]
机构
[1] Josai Univ, Fac Pharmaceut Sci, Sakado, Saitama 35002, Japan
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1998年 / 01期
关键词
D O I
10.1039/a706488h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
AlCl3-mediated decomposition of N-phenoxybenzamide derivatives in dichloromethane mainly leads to regioselective intramolecular migration of the benzamido group from the oxygen to the ortho position of the phenyl group via electron-deficient nitrogen intermediates.
引用
收藏
页码:7 / 11
页数:5
相关论文
共 28 条
[1]  
Abramovitch R. A., 1984, AZIDES NITRENES REAC, P297
[2]   QUINONE IMIDES .24. O-QUINONEMONOIMIDES [J].
ADAMS, R ;
STEWART, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (23) :5876-5880
[3]  
ANDREWS BD, 1969, TETRAHEDRON LETT, P1859
[4]   AROMATIC AMIDES .5. INTRAMOLECULAR HYDROGEN BONDING IN ORTHO SUBSTITUTED ANILIDES [J].
APPLETON, JM ;
ANDREWS, BD ;
RAE, ID ;
REICHERT, BE .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1970, 23 (08) :1667-+
[5]   SELECTIVE DESHIELDING OF AROMATIC PROTONS IN SOME ORTHO-SUBSTITUTED ACETANILIDES [J].
BARTELSKEITH, JR ;
CIECIUCH, RF .
CANADIAN JOURNAL OF CHEMISTRY-BACK YEAR, 1968, 46 (15) :2593-+
[6]   PROTON MAGNETIC RESONANCE SPECTRA OF SOME AROMATIC AMINES AND DERIVED AMIDES [J].
BROWN, RFC ;
RADOM, L ;
STERNHELL, S ;
RAE, ID .
CANADIAN JOURNAL OF CHEMISTRY-BACK YEAR, 1968, 46 (15) :2577-+
[7]  
CHATTAWAY FD, 1999, CHEM BER, V32, P3635
[8]   THE PHENAZINE SERIES .8. THE CONSTITUTION OF THE PIGMENT OF CHROMOBACTERIUM IODINUM [J].
CLEMO, GR ;
DAGLISH, AF .
JOURNAL OF THE CHEMICAL SOCIETY, 1950, (JUN) :1481-1485
[9]  
Derick CG, 1913, J AM CHEM SOC, V35, P1269, DOI 10.1021/ja02198a014
[10]  
EDWARD JT, 1956, J CHEM SOC, P222