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

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 29期

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.

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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