REACTIONS OF AROMATIC NITRO COMPOUNDS WITH BASES

被引：109

作者：

BUCK, P

机构：

[1] Deutsches Institut für Fernstudien, Universität Tübingen

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 1969年 / 8卷 / 02期

关键词：

Bases; Meisenheimer complexes; Nitro compounds;

D O I：

10.1002/anie.196901201

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Aromatic nitro compounds can react in many ways with bases. The reaction path followed depends mainly on the degree of nitration (with a sharp jump from mononitro to di‐ and trinitro compounds) and the base used. Redox reactions or nucleophilic aromatic substitutions predominate with mononitro compounds, whereas Meisenheimer additions together with nucleophilic aromatic substitutions are preferred by dinitro and trinitro compounds; deprotonations are less common. The bromine in nitrobromobenzenes can be replaced by metal at low temperatures. Very weak bases generally give electron donor‐acceptor complexes. Copyright © 1969 by Verlag Chemie, GmbH, Germany

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页码：120 / &

相关论文

共 179 条

[1] PREPARATION + PROPERTIES OF IMIDO INTERMEDIATES ( IMIDOGENS ) [J].

ABRAMOVITCH, RA ;

DAVIS, BA .

CHEMICAL REVIEWS, 1964, 64 (02) :149-&

[2]

[Anonymous], 1967, ANGEW CHEM, V79, P15

[3] ELECTRON SPIN RESONANCE STUDIES OF RADICALS AND RADICAL-IONS IN SOLUTION .4. FURTHER INTERMEDIATES IN REDUCTION OF AROMATIC NITRO- AND NITROSO-COMPOUNDS [J].

AYSCOUGH, PB ;

SARGENT, FP ;

WILSON, R .

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1966, (09) :903-&

[4] ELECTRON SPIN RESONANCE STUDIES OF RADICAL ANIONS .2. AROMATIC NITRO-COMPOUNDS [J].

AYSCOUGH, PB ;

WILSON, R ;

SARGENT, FP .

JOURNAL OF THE CHEMICAL SOCIETY, 1963, (NOV) :5418-&

[5] REDUCTION OF AROMATIC NITRO COMPOUNDS WITH PHOSPHINE [J].

BELLAART, AC .

TETRAHEDRON, 1965, 21 (12) :3285-&

[6] KINETICS OF ISOTOPIC OXYGEN EXCHANGE BETWEEN SUBSTITUTED BENZOIC ACIDS AND WATER [J].

BENDER, ML ;

STONE, RR ;

DEWEY, RS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (02) :319-321

[7] The direct introduction of the amino and substituted amino groups into the aromatic and heterocyclic nucleus VI The action of alkali diphenylamides on some aromatic nitro compounds [J].

Bergstrom, FW ;

Granara, IM ;

Erickson, V .

JOURNAL OF ORGANIC CHEMISTRY, 1942, 7 (01) :98-102

[8]

BERNASCO.C, 1965, TETRAHEDRON LETT, P1083

[9] DER EINFLUSS VON DIMETHYLSULFOXID UND DIOXAN AUF DIE REAKTIONEN VON 2,4-DINITROFLUORBENZOL UND 2,4-DINITROCHLORBENZOL MIT PIPERIDIN IN BENZOL [J].

BERNASCO.CF ;

KAUFMANN, M ;

ZOLLINGE.H .

HELVETICA CHIMICA ACTA, 1966, 49 (08) :2563-&

[10] BASE CATALYSIS OF REACTION OF MORPHOLINE WITH 2,4-DINITROPHENYL PHENYL ETHER IN 10 PERCENT DIOXANE-90 PERCENT WATER [J].

BERNASCONI, CF ;

SCHMID, P .

JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (10) :2953-+

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