p-toluenesulfonic acid catalyzed regiospecific nitration of phenols with metal nitrates

被引：87

作者：

Anuradha, V. ^{[1
]}

Srinivas, P. V. ^{[1
]}

Aparna, P. ^{[1
]}

Rao, J. Madhusudana ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Div Organ Chem 1, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 28期

关键词：

nitration; nickel nitrate; regiospecific; p-TSA;

D O I：

10.1016/j.tetlet.2006.05.017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly regiospecific mononitration of phenols and substituted phenols is accomplished employing a metal nitrate and a catalytic amount of p-toluenesulfonic acid in acetone. An exclusive ortho-selectivity was observed with excellent yields. A variety of metal nitrates were used to obtain o-nitrophenois exclusively in good to excellent yields. The use of p-toluenesulfonic acid is key for the selectivity observed. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：4933 / 4935

页数：3

共 29 条

[21] Nitration and hydroxylation of phenolic compounds by peroxynitrite [J].

Ramezanian, MS ;

Padmaja, S ;

Koppenol, WH .

CHEMICAL RESEARCH IN TOXICOLOGY, 1996, 9 (01) :232-240

[22] Surface-mediated highly efficient regioselective nitration of aromatic compounds by bismuth nitrate [J].

Samajdar, S ;

Becker, FF ;

Banik, BK .

TETRAHEDRON LETTERS, 2000, 41 (42) :8017-8020

[23] Facile, high-yield, regioselective synthesis of ortho-nitrophenols using cerium(IV) ammonium nitrate [J].

Sathunuru, R ;

Rao, UN ;

Biehl, E .

ARKIVOC, 2003, :124-133

[24] Highly efficient nitration of phenolic compounds in solid phase or solution using Bi(NO3)3•5H2O as nitrating reagent [J].

Sun, HB ;

Hua, RM ;

Yin, YW .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (22) :9071-9073

[25] Iron(III)-catalysed nitration of non-activated and moderately activated arenes with nitrogen dioxide molecular oxygen under neutral conditions [J].

Suzuki, H ;

Yonezawa, S ;

Nonoyama, N ;

Mori, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (19) :2385-2389

[26]

Tasneem, 2001, SYNTHETIC COMMUN, V31, P1123

[27] 2-PHASE NITRATION OF PHENOLS .3. THE NITRATION OF ANISOLE [J].

THOMPSON, MJ ;

ZEEGERS, PJ .

TETRAHEDRON, 1991, 47 (41) :8787-8790

[28]

Zolfigol MA, 2001, J CHEM RES, P140

[29] Nitration of phenols under mild and heterogeneous conditions [J].

Zolfigol, MA ;

Ghaemi, E ;

Madrakian, E .

MOLECULES, 2001, 6 (07) :614-620

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