Fluoroalkene chemistry

Timperley, Christopher M.

doi:10.1016/j.jfluchem.2004.02.009

Cited by 10 publications

(4 citation statements)

References 27 publications

(25 reference statements)

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“…Similarly, the lithiated diynyl complex Ru(C"CC"CLi)(dppe)Cp* affords Ru(C"CC"CC 5 F 6 Cl)(dppe)Cp* 7. While phosphorus and sulfur nucleophiles often displace more than one Cl from 2 [7,8], the present studies provided no evidence for the formation of poly-substituted products. Reactions of perfluorocyclopentene with carbon nucleophiles (organolithiums) generally result in substitution of one or both F atoms attached to the C@C double bond, although the reaction with Na[CH(CO 2 Et) 2 ] also afforded a bis(ethoxycarbonyl)vinyl derivative [9].…”

Section: Discussioncontrasting

confidence: 63%

Some ruthenium complexes of fluorinated alkynylcyclopentenes

Bruce

Burgun

Parker

et al. 2010

Journal of Organometallic Chemistry

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Section: Discussioncontrasting

confidence: 63%

Some ruthenium complexes of fluorinated alkynylcyclopentenes

Bruce

Burgun

Parker

et al. 2010

Journal of Organometallic Chemistry

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“…The spectroscopic data for compound 1 have been reported previously. However, in this publication, 1 was obtained from 1,2‐dichlorohexafluorocyclopentene and ArSH using a slightly modified procedure 22 …”

Section: Methodsmentioning

confidence: 99%

“…However, in this publication, 1 was obtained from wileyonlinelibrary.com/journal/pi 1,2-dichlorohexafluorocyclopentene and ArSH using a slightly modified procedure. 22 A 20 mL glass scintillation vial equipped with a magnetic stir bar was charged with 5 mL of solvent and PFCP (0.25 mL, 1.86 mmol). The benzenethiol (0.35 mL, 3.39 mmol) and the amount of base indicated in Table 1 were added last.…”

Section: General Procedures For the Screening Reactions With Arshmentioning

confidence: 99%

Synthesis and characterization of perfluorocyclopentene‐thioether polymers

Bishop,

Balmaceda,

Iacono

et al. 2024

Polymer International

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Due to their unique properties and use in high performance materials, the ability to obtain fluorinated polymers utilizing straightforward synthetic methods remains of interest. In this study, we report the facile synthesis of new fluoropolymers via nucleophilic addition of a di‐thiol to perfluorocyclopentene. Initially, model studies were completed with perfluorocyclopentene and benzenethiol and TMS‐protected benzenethiol to identify the optimal reaction conditions for the polymerization. These reaction conditions were then utilized to prepare perfluorocyclopentene‐thioether polymers from perfluorocyclopentene and 4, 4′‐thiobisbenzenethiol. The isolated polymers had molecular weight distributions consistent with step‐growth polymers and 19F NMR spectroscopy revealed that the addition of the nucleophile to perfluorocyclopentene was controlled. Analysis by differential scanning calorimetry showed that the polymers were amorphous with glass transition temperatures around 65 °C. Thermogravimetric analysis in both air and nitrogen showed an initial degradation temperature around 370 °C, while the air analysis produced an additional plateau with a degradation temperature near 592 °C. This is the first known report of utilizing perfluorocyclopentene for the preparation of perfluorinated‐thioether polymers.This article is protected by copyright. All rights reserved.

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“…This behavior can be explained by the enhanced affinity of hexafluorocyclobutene towards S-nucleophilic center which has been studied by Timperley. [24] Knowledge about this side reaction helps in the design and optimization of multistep synthesis yielding photoswitchable sulfone-based fluorophores.…”

Section: Design and Synthesis Of Cyclobutene Derivativesmentioning

confidence: 99%

Di(benzothienyl)cyclobutenes: Toward Strained Photoswitchable Fluorophores

et al. 2020

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Bis(benzothienyl)ethene sulfones are very interesting molecules for super-resolution microscopy due to their photoswitching properties. However, functionalization of the 'classical' bis (benzothienyl)ethene sulfones with a five-membered central ring leads to significant decrease of quantum yields of photoconversion of the fluorescent closed form of the dye to the non-fluorescent open form that limits their application in microscopy. Here, we designed and synthesized diarylethenes with a fluorinated four-membered central ring that adds extra strain to the closed form of the dye. The reaction mechanism of their formation was studied, and byproducts formed upon structural rearrangement of the benzothiophene fragment were characterized. The photochromic properties of the new molecules were investigated by NMR and absorption spectroscopy. Some of these compounds show enhanced tendency to ring opening and have quantum yields of the ring-opening reaction in the range of 0.2-0.5.

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Fluoroalkene chemistry

Cited by 10 publications

References 27 publications

Some ruthenium complexes of fluorinated alkynylcyclopentenes

Some ruthenium complexes of fluorinated alkynylcyclopentenes

Synthesis and characterization of perfluorocyclopentene‐thioether polymers

Di(benzothienyl)cyclobutenes: Toward Strained Photoswitchable Fluorophores

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