A Practical Three-Step Synthesis of Vinylferrocene

Plevová, Kristína; Mudráková, Brigita; Šebesta, Radovan

doi:10.1055/s-0036-1589142

Cited by 11 publications

(2 citation statements)

References 21 publications

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“…Vinylferrocene was prepared from ferrocene according to an efficient three‐step protocol reported by Šebesta and co‐workers [24] . All other reagents used in this work were of the best commercial grade available and used without further purification.…”

Section: Methodsmentioning

confidence: 99%

Catalyst‐Free Regioselective 1,2‐Diheterofunctionalization of Vinylferrocene

García‐Martínez,

Crespo,

González

et al. 2023

Eur J Inorg Chem

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In this study, we report a catalyst‐free aminohalogenation process applied to vinylferrocene, employing N‐halosuccinimides (NXS; X=Cl, Br, I) as dual nitrogen and halogen sources. This 1,2‐diheterofunctionalization reaction takes place with complete regioselectivity, wherein the terminal carbon atom of the vinyl group selectively reacts with the electrophilic halogenating reagent, resulting in the formation of a cationic intermediate, which is subsequently captured by the succinimide anion. The structure of the key cationic intermediate was studied using theoretical methods. This intermediate can react with alternative nucleophiles, enabling a three‐component strategy for the synthesis of novel 1,2‐diheterofunctionalized ferrocene derivatives.

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Section: Methodsmentioning

confidence: 99%

Catalyst‐Free Regioselective 1,2‐Diheterofunctionalization of Vinylferrocene

García‐Martínez,

Crespo,

González

et al. 2023

Eur J Inorg Chem

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“…Octamethylcyclotetrasiloxane (D 4 , 98%), 1,3,5,7-tetramethylcyclotetrasiloxane (H 4 D 4 , 98%), 1,1,3,3-tetramethyl-1,3-divinyldisiloxane (98%), 1,3,3,5,5,7,7-heptamethylcyclotetrasiloxane (HD 4 , 95%), and platinum (0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex 0.1 M solution in xylene were purchased from Abcr GmbH (Karlsruhe, Germany) and utilized as received. Vinylferrocene was synthesized from ferrocene (98%, Shanghai Macklin Biochemical Co., Shanghai, China) according to the known three-step procedures [54,66]. Previously described substances were analyzed by nuclear magnetic resonance (NMR) spectroscopy before being used.…”

Section: Methodsmentioning

confidence: 99%

Self-Healing Redox-Active Coatings Based on Ferrocenyl-Containing Polysiloxanes

et al. 2023

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The known ferrocenyl-containing silicone materials have redox activity and electrical conductivity at the level of antistatic materials, but they are incapable of self-healing due to their irreversible cross-linking, which significantly reduces their application area. The development of novel self-healing ferrocenyl-containing silicone rubbers (FSRs) is a promising area of research that extends the possibilities of their application as protective coatings. In this work, a new method was developed to synthesize FSRs with different ferrocenyl unit content (25 and 50 mol.%) by anionic copolymerization of cyclic octamethylcyclotetrasiloxane (D4), cyclic tetraferrocenyl-substituted 1,3,5,7-tetramethyltetrasiloxane (Fc4D4), and bicyclic cross-linking agent (bis-D4). The optimal concentrations of the cross-linking agent and ferrocenyl-substituted unit content for FSRs are 5 wt.% and 25 mol.%, respectively. The FSRs exhibit tensile strength and elongation at break up to 0.1 MPa and 215%. The FSRs possess both self-healing at room and/or elevated temperatures (100 °C) and redox activity (Fc/Fc+ transformations at E0 = 0.43 V) and conductivity at the antistatic level (ca. 10−10–10−11 S·cm−1). The thermal properties of the FSRs were studied. The proposed approach is relevant for the creation of new functional silicone materials as flexible, self-healing, and antistatic protective coatings.

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Synthesis of ferrocenyl‐containing silicone rubbers via platinum‐catalyzedSi–Hself‐cross‐linking

Deriabin

Lobanovskaia

Kirichenko

et al. 2019

Applied Organom Chemis

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Self‐cross‐linkable ferrocenyl‐containing polymethylhydrosiloxanes were synthesized. Karstedt's catalyst and cis‐[PtCl2(BnCN)2] were examined as cross‐linking catalysts at room temperature for the reaction between Si–H groups of the ferrocenyl‐containing polymethylhydrosiloxanes. Cis‐[PtCl2(BnCN)2] is an effective catalyst that allows cross‐linked ferrocenyl‐containing silicones (silicone rubbers) to be obtained with no visible mechanical defects (bubbles or cracks) compared with Karstedt's catalyst. The ferrocene content of the ferrocenyl‐containing silicone rubbers was found to be approximately 50 wt.% by energy‐dispersive X‐ray analysis. Compared with cross‐linked non‐modified polymethylhydrosiloxanes, the ferrocenyl‐containing silicone rubbers exhibited improved tensile properties (the tensile strength increased from 0.47 to 0.75 MPa) and a 1.5–2.5 times lower cross‐linking degree. The surface resistivity of the ferrocenyl‐containing silicone rubbers (50 wt.% ferrocenyl units) was approximately 7 × 109 Ω/□, which was 10,000 times lower than that of pure polymethylhydrosiloxane. The obtained flexible electroactive ferrocenyl‐containing silicone rubbers can potentially be applied as coatings for electronic and electrostatic‐sensitive devices, interfaces, and sensors.

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A Practical Three-Step Synthesis of Vinylferrocene

Abstract: An improved, short and efficient synthesis of vinylferrocene is reported. This three-step synthesis includes Friedel–Crafts acylation, reduction, and a one-pot mesylation/elimination step to afford the target compound in 62% yield over three steps.

Cited by 11 publications

References 21 publications

Catalyst‐Free Regioselective 1,2‐Diheterofunctionalization of Vinylferrocene

Catalyst‐Free Regioselective 1,2‐Diheterofunctionalization of Vinylferrocene

Self-Healing Redox-Active Coatings Based on Ferrocenyl-Containing Polysiloxanes

Synthesis of ferrocenyl‐containing silicone rubbers via platinum‐catalyzedSi–Hself‐cross‐linking

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