VICARIOUS NUCLEOPHILIC HYDROXYLATION OF AROMATIC NITRO-COMPOUNDS WITH ORGANIC HYDROPEROXIDES

被引：12

作者：

BROSE, T ^{[1
]}

HOLZSCHEITER, F ^{[1
]}

MATTERSTEIG, G ^{[1
]}

PRITZKOW, W ^{[1
]}

VOERCKEL, V ^{[1
]}

机构：

[1] TECH UNIV MERSEBURG,DEPT CHEM,GEUSAER STR,O-4200 MERSEBURG,GERMANY

来源：

JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG | 1992年 / 334卷 / 06期

关键词：

D O I：

10.1002/prac.19923340609

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Nitrobenzene, alpha-nitronaphthalene, m-dinitrobenzene, 1,3,5-trinitrobenzene, m-nitrobenzophenone, m-nitrobenzonitrile, methyl m-nitrobenzoate and m-nitro diphenylsulphone can be hydroxylated with cumene or tert-butyl hydroperoxide in dipolar aprotic solvents in the presence of strong bases. The hydroxyl group is introduced preferably in p-position to the nitro group. Attempts to hydroxylate benzophenone, anthraquinone, 2-ethyl anthraquinone, anthraquinone 2-sulphonate, benzonitrile and diphenyl sulphone under the same conditions failed. 1-Nitroanthraquinone delivered 1-hydroxy, 1,2-dihydroxy and 1,4-dihydroxy anthraquinone.

引用

页码：497 / 504

页数：8

共 39 条

[1] AN IMPROVED METHOD OF NITRATING AROMATIC ORTHO-HYDROXY-CARBOXYLIC ACIDS AND THEIR ESTERS [J].

BARANY, HC ;

PIANKA, M .

JOURNAL OF THE CHEMICAL SOCIETY, 1946, (OCT) :965-966

[2] NUCLEOPHILIC DISPLACEMENT OF AROMATIC NITRO-GROUPS [J].

BECK, JR .

TETRAHEDRON, 1978, 34 (14) :2057-2068

[3]

BEISER WH, 1922, J AM CHEM SOC, V44, P2302

[4]

Berger S., 1984, 13C NMR SPEKTROSKOPI

[5]

BLANKSMA JJ, 1947, RECL TRAV CHIM PAY B, V66, P353

[6]

Bremser W., 1987, CARBON 13 NMR SPECTR

[7]

CLARKE HT, 1941, ORG SYNTH, V1, P541

[8]

DYYOUNG W, 1952, J ORG CHEM, V17, P1221

[9] SYNTHESIS OF AROMATIC FLUORO COMPOUNDS BY NUCLEOPHILIC EXCHANGE OF NITRO-GROUPS BY FLUORIDE [J].

EFFENBERGER, F ;

STREICHER, W .

CHEMISCHE BERICHTE, 1991, 124 (01) :157-162

[10] NUCLEOPHILIC-SUBSTITUTION OF NITRITE IN NITROBENZENES, NITROBIPHENYLS, AND NITRONAPHTHALENES [J].

EFFENBERGER, F ;

KOCH, M ;

STREICHER, W .

CHEMISCHE BERICHTE, 1991, 124 (01) :163-173

← 1 2 3 4 →