Nucleophilic substitution of hydrogen in heterocyclic chemistry

被引:365
作者
Makosza, M [1 ]
Wojciechowski, K [1 ]
机构
[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw 42, Poland
关键词
D O I
10.1021/cr020086+
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Nucleophiles can react with electron-deficient arenes in a variety of ways. The most important of them is addition to the ring to form anionic σ-adducts. This review covers early examples of reactions that proceed via addition of nucleophiles to electron-deficient arenes in positions occupied with hydrogen followed by transformations of the formed σH-adducts.
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页码:2631 / 2666
页数:36
相关论文
共 352 条
[1]   On the mechanism of the dimethyldioxirane oxidation of σH adducts (Meisenheimer complexes) generated from nitroarenes and carbanions [J].
Adam, W ;
Makosza, M ;
Zhao, CG ;
Surowiec, M .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (04) :1099-1101
[2]   DMD oxidation of in-situ-generated σH adducts derived from nitroarenes and the carbanion of 2-phenylpropionitrile to phenols:: The first direct substitution of a nitro by a hydroxy group [J].
Adam, W ;
Makosza, M ;
Stalinski, K ;
Zhao, CG .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (13) :4390-4391
[3]   ON 1-(3,5-DIMETHYLPYRAZOLYL)PHENAZINYL-2-NITRENE [J].
ALBINI, A ;
BETTINETTI, GF ;
MINOLI, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (01) :4-7
[4]   REACTIVITY OF N,N-DIALKYLAMIDE ENOLATE IONS - ARYLATION OF 1-METHYL-2-PYRROLIDINONE ENOLATE IONS BY THE SRN1 MECHANISM [J].
ALONSO, RA ;
RODRIGUEZ, CH ;
ROSSI, RA .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (25) :5983-5985
[5]  
ANGELI A, 1901, GAZZ CHIM ITAL, V31, P27
[6]  
ARMILLOTTA N, 1982, SYNTHESIS-STUTTGART, P836
[7]  
ATKINSON JG, 1979, TETRAHEDRON LETT, V20, P2657
[8]   The products of vicarious nucleophilic substitution and annelation in the reactions of α-haloalkyl carbanions with benzonaphthyridines and their N-oxides [J].
Bachowska, B .
MONATSHEFTE FUR CHEMIE, 2002, 133 (08) :1071-1076
[9]   Vicarious nucleophilic substitution of hydrogen and formation of aziridine rings in reactions of benzonaphthyridines and their N-oxides with chloromethyl phenyl sulfone [J].
Bachowska, B ;
Zujewska, T .
MONATSHEFTE FUR CHEMIE, 2001, 132 (07) :849-854
[10]  
BAEYER A, 1880, CHEM BER, V13, P187