Electrochemical oxidation of tetracyclones and tetraphenylthiophene-S-oxide

Iniesta, Jesús; Alcock, Hannah; Walton, David J.; Watanabe, Masataka; Mataka, Shuntarō; Thiemann, Thies

doi:10.1016/j.electacta.2006.03.001

Cited by 13 publications

(8 citation statements)

References 47 publications

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“…S-oxides show oxidative electrochemistry at platinum in MeCN/Bu 4 NPF 6 [97]. The electrochemical oxidation of tetraphenylthiophene S-oxide under the above conditions leads mainly to the formation of diphenylacylstilbene [98]. Here, more effort needs to be invested to identify the electro-oxidative transformations of other thiophene S-oxides.…”

Section: Chalcogen Chemistrymentioning

confidence: 99%

Thiophene S-Oxides

Thiemann

Dongol

2019

Chalcogen Chemistry

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Thiophene S-oxides constitute a class of molecules that have been studied in more detail only recently. Their existence as intermediates in the peracid mediated oxidation of thiophenes to thiophene S,S-dioxides, however, has been known over some time. Over the last 20 years, a larger number of thiophene S-oxides have been prepared and isolated in pure form. Thiophene S-oxides have been found to be good dienes in [4 + 2]-cycloaddition reactions, where they react with electron-poor, electron-neutral and electron-rich dienophiles with high syn π-facial stereoselectivity. Thiophene S-oxides have been found to be metabolites of thienyl-containing pharmaceuticals such as the anti-platelet drugs ticlopidine and clopidogrel. The chapter gives an overview of the preparation and reactivity of this class of compounds.

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Section: Chalcogen Chemistrymentioning

confidence: 99%

Thiophene S-Oxides

Thiemann

Dongol

2019

Chalcogen Chemistry

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“…67 Preparatively, electrochemical reduction of thiophene Soxides has been shown to lead to the respective thiophenes (Scheme 24). 69 Sonoirradiation of 65a at both 40 kHz and 850 kHz leads to a 10-fold increase in oxidation current with loss of definition of the two oxidation waves. It has been shown that in acetonitrile, tetraphenylthiophene S-oxide 65a reverts to dibenzoylstilbene 74 at 2.1V vs. SCE (Ptelectrode, Bu 4 NPF 6 as electrolyte) and to a mixture of the latter and the unstable sulfenic acid 75 (x = 0) at 1.6V versus SCE (Scheme 25).…”

Section: Electrochemical Oxidation and Reduction Of Thiophenes Thiopmentioning

confidence: 99%

Photochemical and Electrochemical Oxygenation of Thiophenes, Benzo[b]Thiophenes and Dibenzothiophenes; Photochemical and Electrochemical Behaviour of Their Oxygenated Intermediates and Products

Thiemann

2010

Journal of Chemical Research

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Prof. Dr. Thies Thiemann received his chemical education at the universities of Hamburg and Tuebingen, Germany. After obtaining a PhD degree in organic chemistry at the University of Hamburg, he moved to Japan for his postdoctorate at Kyushu University, Fukuoka. Thies has also worked at joined the chemistry faculty of the United Arab Emirates University in Al Ain, Abu Dhabi. His main focus is on organic synthetic chemistry, especially in the areas of steroidal and heterocyclic chemistry. He is author/co-author of over 150 papers, nine reviews, three book chapters and five patents. S-oxides and benzo[b]thiopheneS,S-dioxides 672 6. Photochemistry of thiophene S-oxides 675 7. Electrochemical oxidation and reduction of thiophenes, thiophene S-oxides and related compounds 675 8. Conclusions 676 9. References 678The photooxygenation of thiophenes, benzo[b]thiophenes and dibenzothiophenes is discussed, especially in view of the oxidative removal of these S-containing contaminants from fuels. Furthermore, the photochemistry of the intermediates and the products from these processes is detailed. Finally, an account is given of the electrooxidation of thiophenes and derivatives to the corresponding sulfoxides and sulfones as well as of the electrochemical behaviour of the intermediate thiophene S-oxides.

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“…[18][19][20][21] While reduction of CPDs led to a fairly stable radical anion species in absence of protons (Figure 1), electro-oxidation has been shown to yield in α-pyrones. [21,22] In the course of our efforts for the development of organic molecules acting as suitable energy storage materials, [23] we got interested in CPDs as a member of the carbonyl family, which recently turned to a promising class of energy storage compounds. [24][25][26] Herein, we present the synthesis of a series of tetraaryl cyclopentadienones aiming to readdress phenyl and heterocyclic substitution effects on both available electrochemical window as well as photophysical properties.…”

Section: Introductionmentioning

confidence: 99%

“…[ 18–21 ] While reduction of CPDs led to a fairly stable radical anion species in absence of protons (Figure 1), electro‐oxidation has been shown to yield in α‐pyrones. [ 21,22 ]…”

Section: Introductionmentioning

confidence: 99%

Tetraaryl Cyclopentadienones: Experimental and Theoretical Insights into Negative Solvatochromism and Electrochemistry

Meitinger¹,

Mengele²,

Witas³

et al. 2020

Eur J Org Chem

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The synthesis of a series of tetraaryl cyclopentadienones comprising different substitution patterns is reported. Their photophysical and electrochemical properties are investigated by UV/Vis spectroscopy and cyclic voltammetry as well as by supporting quantum chemical simulations and reveal a distinct effect of substituents on the redox behavior of the molecules as well as the absorption properties of this class of compounds. While electrochemical data display a shift in reduction potential of up to 200 mV between the differently substituted cyclopentadienones, their photophysical investigations in differently polar solvents suggest a negative solvatochromic effect, although protic solvents induce a bathochromic shift. Crystal structure analyses of some derivatives confirm similarity with related cyclopentadienones while providing insight into intermolecular C–H···O and C–H···π interactions in the solid state.

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Electrochemical oxidation of tetracyclones and tetraphenylthiophene-S-oxide

Cited by 13 publications

References 47 publications

Thiophene S-Oxides

Thiophene S-Oxides

Photochemical and Electrochemical Oxygenation of Thiophenes, Benzo[b]Thiophenes and Dibenzothiophenes; Photochemical and Electrochemical Behaviour of Their Oxygenated Intermediates and Products

Tetraaryl Cyclopentadienones: Experimental and Theoretical Insights into Negative Solvatochromism and Electrochemistry

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