Synthesis and some reactions of ferrocenylacetylenes

Doisneau, Gilles; Balavoine, G.; Fillebeen-Khan, Tauqir

doi:10.1016/0022-328x(92)80026-t

Cited by 168 publications

(113 citation statements)

References 6 publications

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“…The electrochemical experiments were carried out using a Potentiostat/Galvanostat (BHP 2061-C Electrochemical Analysis System, Behpajoh, Iran) coupled with a Pentium IV personal computer connected to a HP laser jet 6L printer. Ethynylferrocene was prepared according to known procedure 22,31 from acetyl ferrocene. According to the literature, ethynylferrocene has a reversible electrochemical behavior showing an E 1/2 (half wave potential) about 0.5 V/Ag/AgCl in an aqueous solution 22 .…”

Section: Materials and Equipmentmentioning

confidence: 99%

Synthesis and electrochemical study of some novel alkynylferrocene derivatives

Hosseinzadeh¹,

Ojani²,

Shabani³

2013

10.5267/j.ccl

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Ferrocene and their derivatives are well-known redox active materials and were extensively used by construction of modified electrodes for the design of electrochemical sensors and biosensors. Substituent derivatization of ferrocene offers the prospect of controlling ferrocene moiety properties such as solubility, stability, reversibility of oxidation wave (important for their role as an electron transfer mediator) and oxidation potential, which is critical in the electrochemical determination of biological compounds. A new series of rigid alkynylferrocene including of 2-ferrocenylethynyl fluoren (3a), 2-ferrocenylethynyl fluoren-9-one (3b), 4-ferrocenylethynyl aniline (3c) and 3-ferrocenylethynyl-1-trifluoromethyl benzene (3d) have been prepared in good yields by Sonogashira coupling reaction. All products were characterized by 1 H and 13 C NMR, FT-IR, and elemental analysis. The redox chemistry of these compounds has been investigated by cyclic voltammetry. The half-wave potential of the terminal ferrocenyl moieties increases progressively in the order of 3c<3a<3b<3d, which is consistent with the electron density on the ferrocenyl unit.

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Section: Materials and Equipmentmentioning

confidence: 99%

Synthesis and electrochemical study of some novel alkynylferrocene derivatives

Hosseinzadeh¹,

Ojani²,

Shabani³

2013

10.5267/j.ccl

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“…Therefore our study started from 1,1'-di(1-propynyl)ferrocene (1). [22] Because of the ready availability of the catalyst we decided to test the Mortreux catalyst system, essentially using hexacarbonylmolybdenum and a phenol derivative in a solvent with a high boiling point. [23][24][25][26][27] The reaction, which would involve metallacyclobutadiene intermediates, [28] was expected to yield oligo(1,1'-ferrocenylidene)ethynylenes.…”

Section: Resultsmentioning

confidence: 99%

“…Compound 1 was prepared according to a published procedure. General procedure (GP): A solution of 1 [22] (262 mg, 1.0 mmol) and the phenol (1.2 mmol) in chlorobenzene (20 mL) was heated at reflux (oil bath 135 8C) for 15 h. After cooling to 25 8C the solvent was removed at reduced pressure. The residue was purified by column chromatography (hexane/dichloromethane 4:1) to give the product as a dark red solid.…”

Section: Methodsmentioning

confidence: 99%

Transannular Addition of Phenols to 1,1′‐Dialkynylferrocenes: Unanticipated Formation of Phenoxy[4]ferrocenophanedienes

Ma¹,

Kühn²,

Hackl³

et al. 2010

Chemistry A European J

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The reaction of some 1,1'-dialkynylferrocenes with a variety of phenols in the presence as well as in the absence of [Mo(CO)(6)] yields good to high yields of phenoxy[4]ferrocenophanedienes. Similar reactivity was observed with a thiophenol and with acetic acid. Reaction under basic reaction conditions led to the formation of the [4]ferrocenophanone 17. The phenoxy[4]ferrocenophanedienes obtained show dynamic behavior as a result of a torsional twist of the carbon bridge as indicated by the (1)H and (13)C NMR spectra. The reaction mechanism is discussed in view of recent related results of Sato et al. as well as of Pudelski et al. A vinyl cation intermediate is postulated in this context, whose relative stability is evident from the mass spectra of the compounds prepared.

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“…[290] Viele Ansätze umfassen den Einsatz von Acetophenon als Ausgangsverbindung sowie die Umwandlung von Aldehyden in terminale Alkine durch Vilsmeier-und Wittig-Reaktionen oder die Dehydratisierung von Acetylferrocenen. [291] Ein direkter Zugang ist die Kupplung von Ferrocen mit einem terminalen Alkin in einer Eintopfreaktion mit DiazotierungArylierung (Schema 63). 1,2-Alkinylierte Ferrocene [292] sind anders als 1,1'-Diethinylferrocen (Bildung von ansa-Ferrocenen) [293] halbwegs stabil.…”

Section: Ferrocenylalkineunclassified

Metall‐Alkinyl‐σ‐Komplexe: Synthesen und Materialien

Long

Williams

2003

Angewandte Chemie

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Metallalkinylkomplexe bergen eine große Anziehungskraft für die Synthesechemie, die Strukturchemie und die Materialwissenschaften, sodass mittlerweile eine Vielzahl von Reaktionen zur M‐CC‐Verknüpfung mit einer ganzen Skala von Übergangsmetall‐ und Alkinylreagentien entwickelt wurde. Einige Methoden sind breit anwendbar, andere beschränken sich auf ein spezielles Metall oder Substrat. Wegen der linearen Geometrie der Alkinyleinheit und ihrem ungesättigten Charakter sind die Metallalkinyle attraktive Bausteine für molekulare Drähte und polymere metallorganische Materialien, die interessante physikalische Eigenschaften wie flüssigkristallines Verhalten, optische Nichtlinearität, Lumineszenz und elektrische Leitfähigkeit aufweisen können. Dieses einzigartige Spektrum an Eigenschaften steht als treibende Kraft hinter der intensiven Erforschung von Metall‐Alkinyl‐σ‐Komplexen. Die Entwicklung und Fortschritte insbesondere der letzten zehn Jahre werden in diesem Aufsatz zusammengefasst.

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Synthesis and some reactions of ferrocenylacetylenes

Cited by 168 publications

References 6 publications

Synthesis and electrochemical study of some novel alkynylferrocene derivatives

Synthesis and electrochemical study of some novel alkynylferrocene derivatives

Transannular Addition of Phenols to 1,1′‐Dialkynylferrocenes: Unanticipated Formation of Phenoxy[4]ferrocenophanedienes

Metall‐Alkinyl‐σ‐Komplexe: Synthesen und Materialien

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