Oxidation of α-alkylbenzyl alcohols catalysed by 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin iron(III) chloride.: Competition between C-H and C-C bond cleavage

被引：26

作者：

Baciocchi, E

Belvedere, S

Bietti, M

机构：

[1] Univ Roma La Sapienza, Dipartimento Chim, I-00185 Rome, Italy

[2] Univ Roma Tor Vergata, Dipartimento Sci & Tecnol Chim, I-00133 Rome, Italy

[3] Univ Roma La Sapienza, Dipartimento Chim, CNR, Ctr Meccanismi Reaz, I-00185 Rome, Italy

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 26期

关键词：

D O I：

10.1016/S0040-4039(98)00863-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The iodosylbenzene promoted oxidation of a number of alpha-alkylbenzyl alcohols catalysed by 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin iron(lll) chloride (Fe(lll)TPFPPCl) leads to the formation of C-H and C-C bond cleavage products, aryl ketones and ben-aldehydes, respectively. It is suggested that the C-H bond cleavage path occurs through a hydrogen atom transfer (HAT) mechanism, whereas C-C bond cleavage products derive from the decomposition of an intermediate complex formed between the iron oxo complex and the alcohol (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：4711 / 4714

页数：4

共 12 条

[1] Baciocchi E, 1998, EUR J ORG CHEM, V1998, P299, DOI 10.1002/(SICI)1099-0690(199802)1998:2<299::AID-EJOC299>3.0.CO
[2] 2-B
[3] de Montellano P.R. Ortiz., 1995, CYTOCHROME P450 STRU
[4] HYDROCARBON BOND-DISSOCIATION ENERGIES
MCMILLEN, DF
GOLDEN, DM
[J]. ANNUAL REVIEW OF PHYSICAL CHEMISTRY, 1982, 33 : 493 - 532
[5] METALLOPORPHYRINS AS VERSATILE CATALYSTS FOR OXIDATION REACTIONS AND OXIDATIVE DNA CLEAVAGE
MEUNIER, B
[J]. CHEMICAL REVIEWS, 1992, 92 (06) : 1411 - 1456
[6] Montanari F., 1994, METALLOPORPHYRIN CAT
[7] BIOMIMETIC OXIDATION WITH MOLECULAR-OXYGEN - SELECTIVE CARBON CARBON BOND-CLEAVAGE OF 1,2-DIOLS BY MOLECULAR-OXYGEN AND DIHYDROPYRIDINE IN THE PRESENCE OF IRON PORPHYRIN CATALYSTS
OKAMOTO, T
SASAKI, K
OKA, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) : 1187 - 1196
[8] SHELDRON RA, 1994, METALLOPORPHYRINS CA
[9] HIGH-YIELD EPOXIDATIONS WITH HYDROGEN-PEROXIDE AND TERT-BUTYL HYDROPEROXIDE CATALYZED BY IRON(III) PORPHYRINS - HETEROLYTIC CLEAVAGE OF HYDROPEROXIDES
TRAYLOR, TG
TSUCHIYA, S
BYUN, YS
KIM, C
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (07) : 2775 - 2781
[10] ALIPHATIC HYDROXYLATION CATALYZED BY IRON(III) PORPHYRINS
TRAYLOR, TG
HILL, KW
FANN, WP
TSUCHIYA, S
DUNLAP, BE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (04) : 1308 - 1312

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