FeCl2py+4 catalyzed transformation of aromatic amines by HOOH under mild conditions

被引:10
作者
Costas, M
Romero, I
Martínez, MA
Llobet, A
Sawyer, DT
Caixach, J
机构
[1] Univ Girona, Dept Quim, E-17071 Girona, Spain
[2] Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA
[3] CSIC, Lab Espectromet Masses, IIQAB, E-08034 Barcelona, Spain
关键词
aromatic amines; hydrogen peroxide; t-butylhydro-peroxide; Fe(III)-pyridine-chloride complex; catalytic oxidations;
D O I
10.1016/S1381-1169(99)00057-6
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
FeCl(2)py(4)(+) is capable of activating HOOH for the selective and efficient (yields range roughly from 50 to 80%) transformation of anilines at room temperature using pyridine as the solvent. Initially, aniline yields mainly nitrosobenzene that in turn reacts with more aniline to form the corresponding azo and azoxybenzene derivatives. Replacing HOOH by t-BuOOH in the system, changes the product distribution dramatically forming only nitrobenzene. Under the same conditions FeCl(2)py(4)(+) efficiently catalyzes the mono-demethylation of N,N'-dimethylaniline by HOOH. (C) 1999 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:49 / 58
页数:10
相关论文
共 46 条
[1]   THE NATURE OF HEME ANILINE INTERACTIONS DURING HEMIN-MEDIATED OXYGEN ACTIVATION AND INSERTION REACTIONS [J].
ADAMS, PA ;
ADAMS, C ;
BERMAN, MC ;
LAWRENCE, MC .
JOURNAL OF INORGANIC BIOCHEMISTRY, 1984, 20 (04) :291-297
[2]   EFFECT OF PHASE-TRANSFER CATALYSIS ON THE SELECTIVITY OF HYDROGEN-PEROXIDE OXIDATION OF ANILINE [J].
BARAK, G ;
SASSON, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (14) :3484-3486
[3]   Models for non-heme oxidation enzymes [J].
Barton, DHR ;
Taylor, DK .
PURE AND APPLIED CHEMISTRY, 1996, 68 (03) :497-504
[4]   The selective functionalization of saturated hydrocarbons .32. Distinction between the Fe-II-Fe-IV and Fe-III-Fe-V manifolds in Gif chemistry. The importance of carboxylic acids for alkane activation. Evidence for a dimeric iron species involved in Gif-type chemistry [J].
Barton, DHR ;
Hu, B ;
Taylor, DK ;
Wahl, RUR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1996, (06) :1031-1041
[5]  
BURCKARD P, 1965, B SOC CHIM FR, P2730
[6]   CRITICAL-REVIEW OF RATE CONSTANTS FOR REACTIONS OF HYDRATED ELECTRONS, HYDROGEN-ATOMS AND HYDROXYL RADICALS (.OH/.O-) IN AQUEOUS-SOLUTION [J].
BUXTON, GV ;
GREENSTOCK, CL ;
HELMAN, WP ;
ROSS, AB .
JOURNAL OF PHYSICAL AND CHEMICAL REFERENCE DATA, 1988, 17 (02) :513-886
[7]   High-resolution solid-state magic angle spinning nuclear magnetic resonance studies on the layered antimony hydrogen phosphate, HSb(PO4)(2)center dot 2H(2)O, and its reaction products with tetrakis(pyridyl)iron(II) chloride [J].
Carlino, S ;
Hudson, MJ ;
Locke, WJ .
JOURNAL OF MATERIALS CHEMISTRY, 1997, 7 (05) :813-819
[8]   OXIDATION OF ORGANIC SUBSTRATES WITH POTASSIUM FERRATE(VI) IN THE PRESENCE OF THE K10 MONTMORILLONITE [J].
DELAUDE, L ;
LASZLO, P ;
LEHANCE, P .
TETRAHEDRON LETTERS, 1995, 36 (46) :8505-8508
[9]   THE OXIDATION OF AMINES WITH PERACETIC ACID [J].
EMMONS, WD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (20) :5528-5530
[10]   BARIUM FERRATE MONOHYDRATE BAFEO4.H2O, A USEFUL OXIDANT FOR THE OXIDATION OF ORGANIC-COMPOUNDS UNDER APROTIC CONDITIONS [J].
FIROUZABADI, H ;
MOHAJER, D ;
ENTEZARIMOGHADAM, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (06) :2185-2189