Electrochemical oxidation of some mesocyclic dithioethers and related compounds

Wilson, George S.; Swanson, Dale D.; Klug, J. T.; Glass, Richard S.; Ryan, Michael D.; Musker, W. Kenneth

doi:10.1021/ja00498a046

Cited by 60 publications

(16 citation statements)

References 1 publication

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“…The lower current function for Ph 2 Se0 was consistent with the results previously obtained for the sulfoxide analogue, 1,1'-sulfinylbisbenzene, which was oxidized by an overall one-electron process.' 4 Similar behavior was observed for Tol 2 Se0 (Fig. 3, solid line).…”

Section: Resultssupporting

confidence: 79%

“…Addition of strong acids to diphenyl sulfoxide has no effect on its oxidation peak, and there was no evidence for the protonation of this species? 4 These results are consistent with the measured aqueous The oxidation of Ph,Se was repeated in the presence of various concentrations of 2,6-di-t-butyl pyridine. No new peaks were observed in the voltammograms, even with a twofold excess of base (Fig.…”

Section: Not Oxidizablesupporting

confidence: 85%

“…1 In cyclic dithia and diselena compounds, the coupling is intramolecular and the product is quite stable.3-6 For example, dithiacyclooctane undergoes a reversible two-electron oxidation to the dication, with a transannular S-S bond. 3 · 4 Similar voltammetry was…”

Section: Introductionmentioning

confidence: 99%

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The Electrochemical Oxidation of Organic Selenides and Selenoxides

Yau

Hack

1997

J. Electrochem. Soc.

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The electrochemical oxidation of alkyl and aryl selenides was investigated in acetonitrile. The oxidation of diphenyl selenide and di(4-methylphenyl) selenide led primarily to the formation of their respective selenoxides, which were identified by exhaustive coulometric oxidation and 1 H and 13 C analysis of the products. The selenoxide itself was not observed in the cyclic voltammetry of the selenide for two reasons: first, the protonation of the selenoxide by the acid formed from the reaction of water with the cation radical and second, the formation of a selenoxide hydrate. The formation of the hydrate with diphenyl selenoxide was verified by isolation of the dimethoxy derivative. In addition to the selenoxide, selenonium compounds, formed by the coupling of the oxidized material, were also observed. The alkyl selenides were generally oxidized at a lower potential than the aryl selenides. This trend is different from the sulfur analogues, where the aryl sulfides are easier to oxidize than their alkyl counterparts. As a result, the difference in their redox potentials is relatively small. These differences may occur because the oxidation of aryl sulfides is more likely to take place on the aromatic ring, which leads to a greater yield of the coupled products (about 100%) when compared to the selenide analogue.

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Section: Resultssupporting

confidence: 79%

Section: Not Oxidizablesupporting

confidence: 85%

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The Electrochemical Oxidation of Organic Selenides and Selenoxides

Yau

Hack

1997

J. Electrochem. Soc.

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“…The saturated C-C and C-H bonds cannot afford redox reaction, hence it can be deduced that thioether bond is the only electrochemical active function group to offering energy storage. The oxidation of thioether had been studied and reported in literatures (Gilbert et al, 1973;Glass et al, 1977Glass et al, , 1990Momose et al, 1987;Musker & Roush, 1978;Musker et al, 1978;Musker, 1980;Symons, 1974;Werst, 1991;Wilson, 1979), which illuminated the formation and existence of thioether cation. Fig.2 Poly(ethene-1,1,2,2-tetrathiol) PETT displays a stable discharge specific capacity value of ca.…”

Section: The Cycling Specific Capacity and Proposed Redox Reactionmentioning

confidence: 99%

“…In addition, solvents are important to the cathode redox reaction. The oxidation of thioether can be facilitated by electro-donating group (Glass, 1977), and thioether cation can be stabilized by electron donation (Wilson et al, 1979). The specific capacity results of thioether polymers were tested with 1, 2-dimethoxyethane and 1, 3-dioxolane mixture as electrolyte.…”

Section: Fig 4 Cycle Life Of Poly[1245-tetrakis(propylthio)benzementioning

confidence: 99%