Electrophilic and nucleophilic aromatic substitution: Analogous and complementary processes

被引:80
作者
Makosza, M
机构
[1] Institute of Organic Chemistry, Polish Academy of Sciences, 01-224 Warsaw
关键词
nitroarenes; carbanions; O-nucleophiles; N-nucleophiles; vicarious substitution; oxidative substitution;
D O I
10.1007/BF01435770
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Analysis of many variants of nucleophilic aromatic substitution of hydrogen proceeding according to an addition-elimination pattern reveals that this is the major reaction pathway, whereas nucleophilic replacement of halogen or another nucleofugal group is the secondary process, i.e., ipso-substitution, In this respect electrophilic and nucleophilic aromatic substitution can be considered as analogous processes.
引用
收藏
页码:491 / 504
页数:14
相关论文
共 70 条
[1]  
[Anonymous], 1991, NUCLEOPHILIC AROMATI
[2]   SOME ASPECTS OF ANIONIC SIGMA-COMPLEXES [J].
ARTAMKINA, GA ;
EGOROV, MP ;
BELETSKAYA, IP .
CHEMICAL REVIEWS, 1982, 82 (04) :427-459
[3]  
BALLESTER M, 1986, SYNTHESIS-STUTTGART, P64
[4]   NOVEL NUCLEOPHILE-DEPENDENT CINE-SUBSTITUTION IN ALPHA-NITROFURANS [J].
BARNES, BJ ;
NEWCOMBE, PJ ;
NORRIS, RK ;
WILSON, K .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (20) :1408-1409
[5]   CONJUGATE ADDITION OF ALKYL-GRIGNARD REAGENTS TO MONONITROARENES [J].
BARTOLI, G .
ACCOUNTS OF CHEMICAL RESEARCH, 1984, 17 (03) :109-115
[6]   A NEW REDOX SYSTEM - TRICHLOROMETHYLARENE-PYRIDINE BASE - ON THE MECHANISM OF THE SYNTHESIS OF N-(4-PYRIDYL)PYRIDINIUM DICHLORIDE [J].
BELENKII, LI ;
PODDUBNYI, IS ;
KRAYUSHKIN, MM .
TETRAHEDRON LETTERS, 1995, 36 (28) :5075-5078
[7]  
BERNASCONI CF, 1980, CHIMIA, V34, P1
[8]   RATIONALIZING THE REGIOSELECTIVITY IN POLYNITROARENE ANIONIC SIGMA-ADDUCT FORMATION - RELEVANCE TO NUCLEOPHILIC AROMATIC-SUBSTITUTION [J].
BUNCEL, E ;
DUST, JM ;
TERRIER, F .
CHEMICAL REVIEWS, 1995, 95 (07) :2261-2280
[9]  
BUNNETT JF, CHEM REV, V49, P275
[10]  
CAREY FA, 1990, ADV ORGANIC CHEM