Synthesis and chemical oxidation of 3-ferrocenylpyrrole and ferrocenyl-substituted triazoles: Iron versus ligand based oxidation

被引：8

作者：

Verschoor-Kirss, Michael ^{[1
]}

Kreisz, Joszef ^{[1
]}

Feighery, William ^{[2
]}

Reiff, William M. ^{[1
]}

Frommen, Christoph M. ^{[1
]}

Kirss, Rein U. ^{[1
]}

机构：

[1] Northeastern Univ, Dept Chem & Chem Biol, Boston, MA 02115 USA

[2] Indiana Univ, Dept Chem, South Bend, IN 46634 USA

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2009年 / 694卷 / 20期

关键词：

Copper catalyzed [3+2] cycloaddition; reactions; Ferrocenyl-1,2,3-triazoles; 3-Ferrocenylpyrrole; Fe-57 Mossbauer spectroscopy; Oxidation of ferrocenes; ANODIC ELECTROCHEMISTRY; CLICK CHEMISTRY; 1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE DPPF; CHALCOGENIDE COMPLEXES; AZIDES; SURFACES; BEHAVIOR; ALKYNES;

D O I：

10.1016/j.jorganchem.2009.06.011

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Copper catalyzed [3+2] cycloaddition reactions between ethynylferrocene and benzylazides yields 1-benzyl-4-ferrocenyl-1.2,3-triazoles (2-5). Reaction between phenylacetylene and azidoferrocene yields 1-ferrocenyl-4-phenyl-1,2,3-triazole (6). Anodic electrochemistry of 2-6 suggests reversibel oxidation at potentials more positive than ferrocene. Chemical oxidation of 2 and 3-ferrocenylpyrrole (1) with dichlorodicyanoquinone (DDQ) yields the salts [2(+center dot)] [DDQ(center dot)] and [1(+center dot)] [DDQ(center dot) ] while Fe-II is oxidized to low-spin Fe-III in [2(+center dot)][DDQ(center dot) ]. Magnetization measurements indicate that [1(+center dot)][DDQ(center dot)] is paramagnetic and cannot be viewed as a simple neutral charge transfer complex reminiscent of the mixed stack diamagnetic [ferrocene]degrees[TCNE]degrees. (C) 2009 Elsevier B.V. All rights reserved.

引用

页码：3262 / 3269

页数：8

共 15 条

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Kirss, Rein U.
Verschoor-Kirss, Michael
Reiff, William M.
Kreisz, Joszef
Feighery, William
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
[2] SYNTHESIS AND OXIDATION POTENTIAL OF 3-FERROCENYLPYRROLE
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[3] Ligand-Enhanced Abiotic Iron Oxidation and the Effects of Chemical versus Biological Iron Cycling in Anoxic Environments
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[5] Novel iron complexes and chelators based on cis,cis-1,3,5-triaminocyclohexane: iron-mediated ligand oxidation and biochemical properties
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[9] Copper-Catalyzed [3+2] Cycloaddition/Oxidation Reactions between Nitro-olefins and Organic Azides: Highly Regioselective Synthesis of NO2-Substituted 1,2,3-Triazoles
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[10] Synthesis of the copolymer of 2,3-di(1-tridecyl)thieno[3,4-b]pyrazine with 3-dodecylthiophene using the chemical oxidation with iron trichloride
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