Document Type

Article

Language

eng

Format of Original

5 p.

Publication Date

6-1997

Publisher

Electrochemical Society

Source Publication

Journal of the Electrochemical Society

Source ISSN

0013-4651

Original Item ID

DOI: 10.1149/1.1837728

Abstract

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 and 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.

Comments

Published version. Journal of the Electrochemical Society, Vol. 144, No. 6 (June 1997): 1952-1957. DOI. © 1997 Electrochemical Society. Used with permission.

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