Epoxidation of styrene with iodosylbenzene in the presence of copper(II) Schiff-base complexes

被引：35

作者：

Zolezzi, S

Spodine, E

Decinti, A ^{[1
]}

机构：

[1] Univ Chile, Fac Ciencias Quim & Farmaceut, Dept Quim Inorgan & Analit, Santiago 233, Chile

[2] Univ Chile, Ctr Invest Interdisciplinaria Avanzada & Ciencias, Santiago, Chile

来源：

POLYHEDRON | 2003年 / 22卷 / 13期

关键词：

salen Cu(II) complexes; Schiff-base ligands; catalytic epoxidation; iodosylbenzene; styrene; Hammett substituent constants;

D O I：

10.1016/S0277-5387(03)00326-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Copper(II) complexes with salen Schiff-base ligands derived from ethylenediamine or (S,S)-1,2-diphenylethylenediamine and salicylaldehyde or 5-methoxy, 5-bromo and 5-nitrosalicylaldehyde have been tested as catalysts for the epoxidation of styrene with iodosylbenzene, in dichoromethane as a solvent. The reactions were followed by gas chromatographic analysis and mass spectrometry. Catalytic activities were found to be dependent upon both the Lewis acidity of the metal complexes and the presence of phenyl substituents on the ethylene moiety. Moderate styrene conversions and epoxide yields were obtained. Pseudo-first-order kinetics was observed for the styrene conversion. Possible reaction mechanisms are outlined. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：1653 / 1658

页数：6

共 22 条

[1] CHROMIUM CATALYZED ASYMMETRIC ALKENE EPOXIDATION - GREATER SELECTIVITY FOR AN E-ALKENE VERSUS ITS Z-ISOMER
BOUSQUET, C
GILHEANY, DG
[J]. TETRAHEDRON LETTERS, 1995, 36 (42) : 7739 - 7742
[2] Enantioselective catalysis of epoxidation by metalloporphyrins: Application to enantioselective synthesis
Campbell, LA
Kodadek, T
[J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1996, 113 (1-2) : 293 - 310
[3] COPPER-ION MEDIATED EPOXIDATION OF OLEFINS BY IODOSYLBENZENE
FRANKLIN, CC
VANATTA, RB
TAI, AF
VALENTINE, JS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (03) : 814 - 816
[4] Unusual solvent-effect in stereochemistry of asymmetric epoxidation using a (Salen)chromium(III) complex as a catalyst
Imanishi, H
Katsuki, T
[J]. TETRAHEDRON LETTERS, 1997, 38 (02) : 251 - 254
[5] Syntheses, characterization, redox behavior and Lewis acidity of chiral nickel(II) and copper(II) Schiff base complexes
Jager, EG
Schuhmann, K
Gorls, H
[J]. INORGANICA CHIMICA ACTA, 1997, 255 (02) : 295 - 305
[6] Synthesis, characterization and catalytic activity of polynuclear manganese complexes of 2,5-dihydroxyterephthalaldehyde for epoxidation of olefins with H2O2
Krishnan, R
Vancheesan, S
[J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2000, 157 (1-2) : 15 - 24
[7] Enantioselective catalytic epoxidation of nonfunctionalized prochiral olefins by dissymmetric chiral Schiff base complexes of Mn(III) and Ru(III) metal ions .2.
Kureshy, RI
Khan, NH
Abdi, SHR
Iyer, P
Bhatt, AK
[J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1997, 120 (1-3) : 101 - 108
[8] Chiral Ru(II) Schiff base complex-catalysed enantioselective epoxidation of styrene derivatives using iodosyl benzene as oxidant. II
Kureshy, RI
Khan, NH
Abdi, SHR
Patel, ST
Iyer, P
[J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 150 (1-2) : 175 - 183
[9] CONDUCTANCE AND ION-PAIR FORMATION OF BIS(2,9-DIMETHYL-1,10-PHENANTHROLINE)COPPER(U) PERCHLORATE .2. IN NITROBENZENE-CARBON TETRACHLORIDE AND METHANOL-CARBON TETRACHLORIDE MIXTURES
MIYOSHI, K
TOMINAGA, T
[J]. JOURNAL OF PHYSICAL CHEMISTRY, 1973, 77 (04) : 519 - 523
[10] CONDUCTANCE AND ION-PAIR FORMATION OF BIS(2,9-DIMETHYL-1,10-PHENANTHROLINE)COPPER(I) PERCHLORATE .3. ACETONITRILE-CARBON TETRACHLORIDE AND WATER-DIOXANE MIXTURES
MIYOSHI, K
TOMINAGA, T
[J]. JOURNAL OF PHYSICAL CHEMISTRY, 1973, 77 (06) : 819 - 821

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