New chemical and stereochemical applications of organoiron complexes

Fatiadi, Alexander J.

doi:10.6028/jres.096.002

Cited by 29 publications

(12 citation statements)

References 1,012 publications

(1,331 reference statements)

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“…Complexes of iron (III) with compounds, such as pyridine [2], calixarenes [3], and lignin model compounds [4] have been mainly utilized as oxidation catalysts. Fatiadi [5] has reviewed chemical and stereochemical applications of organo-iron complexes. Some iron (III) complexes with organic compounds have been investigated with e.g., flumequine [6], yet only for iron (III) determinations in aqueous solutions.…”

Section: Aim Of the Investigationmentioning

confidence: 99%

Spectrophotometric determination of iron (III) catalyst in organic compound chlorinations

Rigas¹,

Doulia²

2021

Technium

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In the science or industrial practice of chemical processes, iron (III) is sometimes used as a catalyst in organic compound chlorinations due to its effectiveness and low cost. Thus, a fast and easy method of determination in the system is useful especially when metallic iron is used as a precursor which is readily converted into iron (III) chloride by the gaseous chlorine used in the chlorination reactor. In the latter case, the determination of the produced catalytically effective iron (III) is a prerequisite for controlling the kinetic progress of chlorination. In this work, a method for the spectrophotometric determination of iron (III) chloride in organic media after complexation with methyl ethyl ketone is investigated. The formation of a strong o-complex of iron (III) with methyl ethyl ketone allows direct determination of iron at 360 nm.Beer’s law is valid up to absorbance 2.42, where the iron (III) concentration is 20.7 mg·L-1, with molar absorptivity (e) equal to 6.532×103 L·mol-1·cm-1 and Sandell’s sensitivity 8.5×10-3 ug·cm- 2. Standing time for color development is of the order of a few seconds and stability of color measurements exceeds 12 months. The method may be used among other applications in organic compounds chlorinations catalyzed by iron. These systems are complicated due to the coexistence of various complexes. Nevertheless, the method proposed being simple, fast, and not depending on the composition of the chlorination mixture and the amount of methyl ethyl ketone added was found to be suitable.

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Section: Aim Of the Investigationmentioning

confidence: 99%

Spectrophotometric determination of iron (III) catalyst in organic compound chlorinations

Rigas¹,

Doulia²

2021

Technium

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“…In recent decades, iron complexes bearing the cyclopentadienyl(dicarbonyl)iron moiety have found numerous applications in organic synthesis. [1][2][3][4][5][6][7][8] For example, cationic dicarbonyl(cyclopentadienyl)alkene-iron complexes were extensively examined in carbon-carbon bond formation, due to the observed activation of the alkenic ligand toward nucleophilic addition. For the construction of five-membered ring skeletons iron-mediated, nonconcerted reactions of allyliron complexes with electron-deficient alkenes were found to be of great potential.…”

Section: Introductionmentioning

confidence: 99%

“…The highly nucleophilic sodium dicarbonyl(cyclopentadienyl)ferrate 2 (Scheme 1) is generally used as precursor to most other iron complexes. [1][2][3][4][5][6][7][8][9] A number of preparations for 2 (M = Na) starting from bis(dicarbonylcyclopentadienyliron) (1) and a reducing agent, such as mercury-sodium amalgam 10 or naphthalene-sodium, 11 have been reported.…”

Section: Introductionmentioning

confidence: 99%

Organoiron Compounds for Selective Organic Transformations

Rück‐Braun¹,

Mikulás²,

Amrhein³

1999

Synthesis

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“…There has been immense interest in the use of iron carbonyl reagents in recent years . The readily accessible HFe(CO) 4 - is a versatile reagent used in many organic transformations 1a.…”

Section: Introductionmentioning

confidence: 99%

New Convenient One-Pot Methods of Conversion of Alkynes to Cyclobutenediones or α,β-Unsaturated Carboxylic Acids Using Novel Reactive Iron Carbonyl Reagents

et al. 1998

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Reactions of NaHFe(CO)4/RX or [HFe3(CO)11]- reagents with alkynes lead to the formation of the corresponding α,β-unsaturated carboxylic acids and/or the cyclobutenediones. The reagent generated in situ using the NaHFe(CO)4/CH3I combination in THF, on reaction with alkynes followed by CuCl2·2H2O oxidation, gives the corresponding cyclobutenediones (27−42%) and α,β-unsaturated carboxylic acids (10−22%), whereas the reagent generated using CH2Cl2 in place of CH3I leads to α,β-unsaturated carboxylic acids (37−60%) and their derivatives (35−55%) at 25 °C. The same reagent system in the presence of acetic acid (4 equiv) yields the corresponding cyclobutenedione (33%). The reaction using Me3SiCl gives the corresponding α,β-unsaturated carboxylic acids (45−54%) at 25 °C and the corresponding cyclobutenediones (51−63%) at 60 °C. Interestingly, the reaction of the [HFe3(CO)11]- species generated using Fe(CO)5/NaBH4/CH3COOH, with alkynes at 25 °C, followed by CuCl2·2H2O oxidation gives the corresponding cyclobutenediones (60−73%). The possible intermediates and pathways for the formation of α,β-unsaturated carboxylic acids and cyclobutenediones are discussed.

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New chemical and stereochemical applications of organoiron complexes

Cited by 29 publications

References 1,012 publications

Spectrophotometric determination of iron (III) catalyst in organic compound chlorinations

Spectrophotometric determination of iron (III) catalyst in organic compound chlorinations

Organoiron Compounds for Selective Organic Transformations

New Convenient One-Pot Methods of Conversion of Alkynes to Cyclobutenediones or α,β-Unsaturated Carboxylic Acids Using Novel Reactive Iron Carbonyl Reagents

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