PORPHINATOIRON-CATALYZED OXYGENATION OF STYRENE IN AQUEOUS-SOLUTION

被引:28
作者
KANO, K [1 ]
TAKAGI, H [1 ]
TAKEUCHI, M [1 ]
HASHIMOTO, S [1 ]
YOSHIDA, Z [1 ]
机构
[1] KYOTO UNIV, KYOTO 606, JAPAN
关键词
D O I
10.1246/cl.1991.519
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A quantitative oxygenation of styrene to 1-phenylethanol is realized in a reaction catalyzed by an iron complex of 5,10,15,20-tetrakis(1-methyl-4-pyridinio)porphine tetrachloride (FeTMPyP) in water at pH 12 containing NaBH4. A plausible mechanism involving a styrene carbanion stabilized by Fe(III)TMPyP as an intermediate is presented.
引用
收藏
页码:519 / 522
页数:4
相关论文
共 17 条
[1]   DIOXYGEN INSERTION INTO IRON(III)-CARBON BONDS - NMR-STUDIES OF THE FORMATION AND REACTIVITY OF ALKYLPEROXO COMPLEXES OF IRON(III) PORPHYRINS [J].
ARASASINGHAM, RD ;
BALCH, AL ;
CORNMAN, CR ;
LATOSGRAZYNSKI, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) :4357-4363
[2]   REACTION OF (MESO-TETRAKIS(2,6-DIMETHYL-3-SULFONATOPHENYL)PORPHINATO)-IRON(III) HYDRATE WITH VARIOUS ACYL AND ALKYL HYDROPEROXIDES IN AQUEOUS-SOLUTION [J].
BALASUBRAMANIAN, PN ;
LEE, RW ;
BRUICE, TC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (23) :8714-8721
[3]   DYNAMICS OF REACTION OF [MESO-TETRAKIS(2,6-DIMETHYL-3-SULFONATOPHENYL)PORPHINATO]-IRON(III) HYDRATE WITH TERT-BUTYL HYDROPEROXIDE IN AQUEOUS-SOLUTION .2. ESTABLISHMENT OF A MECHANISM THAT INVOLVES HOMOLYTIC O-O BOND BREAKING AND ONE-ELECTRON OXIDATION OF THE IRON(III) PORPHYRIN [J].
BALASUBRAMANIAN, PN ;
SMITH, JRL ;
DAVIES, MJ ;
KAARET, TW ;
BRUICE, TC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (04) :1477-1483
[4]   SUICIDE INACTIVATION OF CYTOCHROME-P-450 MODEL COMPOUNDS BY TERMINAL OLEFINS .2. STERIC AND ELECTRONIC EFFECTS IN HEME N-ALKYLATION AND EPOXIDATION [J].
COLLMAN, JP ;
HAMPTON, PD ;
BRAUMAN, JI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (08) :2986-2998
[5]   ASYMMETRIC HYDROXYLATION BY A CHIRAL IRON PORPHYRIN [J].
GROVES, JT ;
VISKI, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (22) :8537-8538
[6]   HYDROXYLATION AND EPOXIDATION CATALYZED BY IRON-PORPHINE COMPLEXES - OXYGEN-TRANSFER FROM IODOSYLBENZENE [J].
GROVES, JT ;
NEMO, TE ;
MYERS, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (04) :1032-1033
[7]  
GROVES JT, 1986, J AM CHEM SOC, V105, P5796
[8]  
JORGENSEN KA, 1987, J AM CHEM SOC, V109, P698
[9]   HEMIN-CATALYZED ADDITION-REACTIONS OF THIOPHENOLS TO STYRENE [J].
KANO, K ;
TAKEUCHI, M ;
HASHIMOTO, S ;
YOSHIDA, Z .
CHEMISTRY LETTERS, 1990, (08) :1381-1384
[10]   HIGH-VALENT RUTHENIUM(IV) AND RUTHENIUM(VI) OXO COMPLEXES OF OCTAETHYLPORPHYRIN - SYNTHESIS, SPECTROSCOPY, AND REACTIVITIES [J].
LEUNG, WH ;
CHE, CM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (24) :8812-8818