EXTRADIOL OXYGENATION OF 3,5-DI-TERT-BUTYLCATECHOL WITH O-2 BY IRON CHLORIDES IN TETRAHYDROFURAN-WATER AS A MODEL REACTION FOR CATECHOL-2,3-DIOXYGENASES

被引:20
作者
FUNABIKI, T
YONEDA, I
ISHIKAWA, M
UJIIE, M
NAGAI, Y
YOSHIDA, S
机构
关键词
D O I
10.1039/c39940001453
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Selective extradiol oxygenation of 3,5-di-tert-butylcatechol 1 with O-2 catalysed by Fe2+ is achieved in THF in the presence of water; the different selectivity obtained by FeCl2 and FeCl3 in THF-H2O and THF-pyridine supports the explanation of the intra- and extra-diol oxygenations by Fe3+ and Fe2+, respectively, as proposed in the enzymatic systems.
引用
收藏
页码:1453 / 1454
页数:2
相关论文
共 9 条
[1]   FUNCTIONAL MODELS FOR CATECHOL 1,2-DIOXYGENASE - THE ROLE OF THE IRON(III) CENTER [J].
COX, DD ;
QUE, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (24) :8085-8092
[2]   CATECHOLATE LMCT BANDS AS PROBES FOR THE ACTIVE-SITES OF NONHEME IRON OXYGENASES [J].
COX, DD ;
BENKOVIC, SJ ;
BLOOM, LM ;
BRADLEY, FC ;
NELSON, MJ ;
QUE, L ;
WALLICK, DE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (07) :2026-2032
[3]   EXTENDED HUCKEL STUDY ON OXYGEN INSERTION INTO THE AROMATIC RING BY MODEL COMPLEXES FOR CATECHOL DIOXYGENASES [J].
FUNABIKI, T ;
INOUE, T ;
KOJIMA, H ;
KONISHI, T ;
TANAKA, T ;
YOSHIDA, S .
JOURNAL OF MOLECULAR CATALYSIS, 1990, 59 (03) :367-371
[4]   STRONG RADICAL CHARACTER OF THE CATECHOLATE LIGAND OF CATECHOLATO(PYRIDINE)IRON COMPLEXES INVOLVED IN THE CATECHOLDIOXYGENASE-MODEL REACTION [J].
FUNABIKI, T ;
KOJIMA, H ;
KANEKO, M ;
INOUE, T ;
YOSHIOKA, T ;
TANAKA, T ;
YOSHIDA, S .
CHEMISTRY LETTERS, 1991, (12) :2143-2146
[5]   OXYGENASE MODEL REACTIONS .1. INTRADIOL AND EXTRADIOL OXYGENATIONS OF 3,5-DI-TERT-BUTYLATECHOL CATALYZED BY (BIPYRIDINE)(PYRIDINE)IRON(III) COMPLEX [J].
FUNABIKI, T ;
MIZOGUCHI, A ;
SUGIMOTO, T ;
TADA, S ;
TSUJI, M ;
SAKAMOTO, H ;
YOSHIDA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (11) :2921-2932
[6]   OXIDATIVE AROMATIC RING CLEAVAGE OF 3,5-DI-TERT-BUTYLCATECHOL, WITH TOTAL INSERTION OF MOLECULAR-OXYGEN, CATALYZED BY 2,2'-BIPYRIDINE-IRON(II) COMPLEX [J].
FUNABIKI, T ;
SAKAMOTO, H ;
YOSHIDA, S ;
TARAMA, K .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (17) :754-755
[7]  
FUNABIKI T, IN PRESS
[8]   MECHANISM OF THE PYROCATECHASE REACTION [J].
HAYAISHI, O ;
KATAGIRI, M ;
ROTHBERG, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (20) :5450-5451
[9]   VARIABLE-TEMPERATURE VARIABLE-FIELD MAGNETIC CIRCULAR-DICHROISM STUDIES OF THE FE(II) ACTIVE-SITE IN METAPYROCATECHASE - IMPLICATIONS FOR THE MOLECULAR MECHANISM OF EXTRADIOL DIOXYGENASES [J].
MABROUK, PA ;
ORVILLE, AM ;
LIPSCOMB, JD ;
SOLOMON, EI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4053-4061