THE FUNCTIONALIZATION OF SATURATED-HYDROCARBONS .31. THE FE(PA)(3)-CATALYZED AND [FE(TPA)CL-2]CLO4-CATALYZED OXIDATIONS OF SATURATED-HYDROCARBONS BY HYDROGEN-PEROXIDE - A COMPARATIVE MECHANISTIC STUDY

被引：28
作者：
BARTON, DHR
BECK, AH
TAYLOR, DK
机构：
[1] Department of Chemistry, Texas A and M University. College Station
来源：
TETRAHEDRON | 1995年 / 51卷 / 18期
关键词：
D O I：
10.1016/0040-4020(95)00204-L
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Fe(pa)(3) and [Fe(tpa)Cl-2]ClO4 catalyzed (pa = picolinic acid, tpa = tris(2-pyridylmethyl)amine) functionalization of saturated hydrocarbons by H2O2 in pyridine/acetic acid follows a common reaction pathway. Regioselectivity studies indicate, that a high valent iron species is responsible for the activation of the alkane. Alkyl hydroperoxides are the precursors for ketone and alcohol formation. Dioxygen provides the oxygen atoms in the alkyl hydroperoxide.
引用
收藏
页码：5245 / 5254
页数：10
相关论文
共 55 条
[1]   THE EFFECT OF LIGAND VARIATION ON THE RATE OF CYCLODODECANE OXIDATION UNDER MODIFIED GO AGG-2 CONDITIONS [J].
ABOUTJAUDET, E ;
BARTON, DHR ;
CSUHAI, E ;
OZBALIK, N .
TETRAHEDRON LETTERS, 1990, 31 (12) :1657-1660
[2]   PYRIDINE DERIVATIVES AS COMPLEX FORMERS .8. PRODUCTION OF A NEW 4 AND A NEW 6 TOOTH LIGAND [J].
ANDEREGG, G ;
WENK, F .
HELVETICA CHIMICA ACTA, 1967, 50 (08) :2330-&
[3]  
ANDERSSON KK, 1991, NEW J CHEM, V15, P411
[4]   IRON CATALYZED INSERTION OF SULFUR INTO THE NONACTIVATED C-H BOND [J].
BALAVOINE, G ;
BARTON, DHR ;
GREF, A ;
LELLOUCHE, I .
TETRAHEDRON, 1992, 48 (10) :1883-1894
[5]   THE FE-II-FE-IV AND FE-III-FE-V MANIFOLDS IN AN EXPANDED WORLD OF GIF CHEMISTRY [J].
BARDIN, C ;
BARTON, DHR ;
HU, B ;
ROJASWAHL, R ;
TAYLOR, DK .
TETRAHEDRON LETTERS, 1994, 35 (32) :5805-5808
[6]   PERESTERS .5. DI-TERT-BUTYLPEROXYOXALATE [J].
BARTLETT, PD ;
BENZING, EP ;
PINCOCK, RE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (07) :1762-1768
[7]  
Barton D. H. R., 1989, ACTIVATION FUNCTIONA, P281
[8]   MECHANISM OF THE SELECTIVE FUNCTIONALIZATION OF SATURATED-HYDROCARBONS BY GIF SYSTEMS - RELATIONSHIP WITH METHANE MONOOXYGENASE [J].
BARTON, DHR ;
CSUHAI, E ;
DOLLER, D ;
OZBALIK, N ;
BALAVOINE, G .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1990, 87 (09) :3401-3404
[9]  
BARTON DHR, 1991, TETRAHEDRON, V47, P6561
[10]   DIRECT CONVERSION OF SATURATED-HYDROCARBONS INTO PHENYLSELENO DERIVATIVES [J].
BARTON, DHR ;
BOIVIN, J ;
LECOUPANEC, P .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (18) :1379-1381
123456