MECHANISM OF ARENE HYDROXYLATION BY VANADIUM PICOLINATO PEROXO COMPLEXES

被引：41

作者：

BONCHIO, M ^{[1
]}

CONTE, V ^{[1
]}

DIFURIA, F ^{[1
]}

MODENA, G ^{[1
]}

MORO, S ^{[1
]}

机构：

[1] UNIV PADUA,CNR,CTR STUDIO MECCANISMI REAZ ORGAN,DIPARTIMENTO CHIM ORGAN,I-35131 PADUA,ITALY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 21期

关键词：

D O I：

10.1021/jo00100a029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The mechanism of the reaction of VO(O-2)PIC(H2O)(2) (PIC = picolinic acid anion) with benzene and substituted benzenes in CH3CN, affording the corresponding phenols together with dioxygen, has been further investigated. The reaction is a radical chain process whose initiation produces the actual oxidant which may be described as a radical anion derived from the peroxovanadium complex, possessing, however, a marked electrophilic character. In the propagation steps such species react either with the original peroxo complex yielding dioxygen or with the aromatic substrates affording phenols via the formation of an intermediate.

引用

页码：6262 / 6267

页数：6

共 29 条

[1] APPLICATION OF THE THIANTHRENE 5-OXIDE MECHANISTIC PROBE TO PEROXOMETAL COMPLEXES
BALLISTRERI, FP
TOMASELLI, GA
TOSCANO, RM
CONTE, V
DIFURIA, F
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) : 6209 - 6212
[2] SOME OBSERVATIONS ON THE PI-COMPLEX OF CL ATOMS WITH BENZENE
BENSON, SW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) : 6969 - 6974
[3] BERTRAND MP, 1976, TETRAHEDRON LETT, P3451
[4] HYDROXYLATION OF AROMATICS WITH HYDROGEN-PEROXIDE CATALYZED BY VANADIUM(V) PEROXOCOMPLEXES
BIANCHI, M
BONCHIO, M
CONTE, V
COPPA, F
DIFURIA, F
MODENA, G
MORO, S
STANDEN, S
[J]. JOURNAL OF MOLECULAR CATALYSIS, 1993, 83 (1-2): : 107 - 116
[5] BONACICKOUTECKY V, 1977, J AM CHEM SOC, V99, P872
[6] EVIDENCE OF A SN2-SET CONTINUUM IN THE OXIDATION OF ORGANIC SULFIDES BY PEROXOVANADIUM COMPLEXES
BONCHIO, M
CONTE, V
DIFURIA, F
MODENA, G
PADOVANI, C
SIVAK, M
[J]. RESEARCH ON CHEMICAL INTERMEDIATES, 1989, 12 (02) : 111 - 124
[7] CORRELATION BETWEEN ONE-ELECTRON REDUCTION AND OXYGEN-OXYGEN BOND STRENGTH IN D(O) TRANSITION-METAL PEROXO COMPLEXES
BONCHIO, M
CONTE, V
DIFURIA, F
MODENA, G
MORO, S
CAROFIGLIO, T
MAGNO, P
PASTORE, P
[J]. INORGANIC CHEMISTRY, 1993, 32 (25) : 5797 - 5799
[8] NATURE OF THE RADICAL INTERMEDIATES IN THE DECOMPOSITION OF PEROXOVANADIUM SPECIES IN PROTIC AND APROTIC MEDIA
BONCHIO, M
CONTE, V
DIFURIA, F
MODENA, G
MORO, S
EDWARDS, JO
[J]. INORGANIC CHEMISTRY, 1994, 33 (08) : 1631 - 1637
[9] METAL CATALYSIS IN OXIDATION BY PEROXIDES .31. THE HYDROXYLATION OF BENZENE BY VO(O2)(PIC)(H2O)2 - MECHANISTIC AND SYNTHETIC ASPECTS
BONCHIO, M
CONTE, V
DIFURIA, F
MODENA, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (18) : 4368 - 4371
[10] BONCHIO M, 1961, DIOXYGEN ACTIVATION, P497

← 1 2 3 →