Oxidation of N-methyl-9-t-butylacridane by iodosylbenzene catalyzed by tetrakis(pentafluorophenyl) porphyrin iron(III).: A tool to investigate the mechanism of the oxidative N-demethylation of aromatic tertiary amines.

被引:9
作者
Baciocchi, E
Lapi, A
机构
[1] Univ Rome La Sapienza, Dipartimento Chim, I-00185 Rome, Italy
[2] Univ Rome La Sapienza, CNR, Ctr Studio Meccan Reaz, I-00185 Rome, Italy
关键词
D O I
10.1016/S0040-4039(99)01023-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The PhIO promoted oxidation of N-methyl-9-t-butylacridane (1) catalyzed by tetrakis(pentafluorophenyl) porphyrin iron(III) leads first to 9-t-butylacridane and then to acridine. It is suggested that 1 can represent a reliable machanistic probe to detect the intervention of radical cations in the oxidation of aromatic amines. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5425 / 5428
页数:4
相关论文
共 17 条
[1]   FORMAL HYDRIDE TRANSFER FROM NADH ANALOGS - 1-BENZYL-4-TERT-BUTYL-1,4-DIHYDRONICOTINAMIDE AS A MECHANISTIC PROBE [J].
ANNE, A ;
MOIROUX, J ;
SAVEANT, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10224-10230
[2]   Thermodynamic control in ion radical cleavages through out-of-cage diffusion of products. Dynamics of C-C fragmentation in cation radicals of tert-butylated NADH analogues and other ion radicals [J].
Anne, A ;
Fraoua, S ;
Moiroux, J ;
Saveant, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (16) :3938-3945
[3]  
Anne A, 1998, J PHYS ORG CHEM, V11, P774, DOI 10.1002/(SICI)1099-1395(1998110)11:11<774::AID-POC40>3.0.CO
[4]  
2-T
[5]   Kinetic deuterium isotope effect profiles and substituent effects in the oxidative N-demethylation of N,N-dimethylanilines catalyzed by tetrakis(pentafluorophenyl)porphyrin iron(III) chloride [J].
Baciocchi, E ;
Lanzalunga, O ;
Lapi, A ;
Manduchi, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (23) :5783-5787
[6]  
de Montellano P.R. Ortiz., 1995, CYTOCHROME P450 STRU
[7]   AMINIUM CATION-RADICAL MECHANISM PROPOSED FOR MONOAMINE-OXIDASE-B CATALYSIS - ARE THERE ALTERNATIVES [J].
EDMONDSON, DE .
XENOBIOTICA, 1995, 25 (07) :735-753
[8]   Mechanisms of N-demethylations catalyzed by high-valent species of heme enzymes: Novel use of isotope effects and direct observation of intermediates [J].
Goto, Y ;
Watanabe, Y ;
Fukuzumi, S ;
Jones, JP ;
Dinnocenzo, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (41) :10762-10763
[9]   Evidence for a 1-electron oxidation mechanism in N-dealkylation of N,N-dialkylanilines by cytochrome P450 2B1 - Kinetic hydrogen isotope effects, linear free energy relationships, comparisons with horseradish peroxidase, and studies with oxygen surrogates [J].
Guengerich, FP ;
Yun, CH ;
Macdonald, TL .
JOURNAL OF BIOLOGICAL CHEMISTRY, 1996, 271 (44) :27321-27329
[10]   CHEMICAL MECHANISMS OF CATALYSIS BY CYTOCHROMES-P-450 - A UNIFIED VIEW [J].
GUENGERICH, FP ;
MACDONALD, TL .
ACCOUNTS OF CHEMICAL RESEARCH, 1984, 17 (01) :9-16