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Anodic oxidation of diphenyldiselenide in acetonitrile

✍ Scribed by Atsutaka Kunai; Junji Harada; Jinko Izumi; Hisaaki Tachihara; Kazuo Sasaki

Publisher
Elsevier Science
Year
1983
Tongue
English
Weight
560 KB
Volume
28
Category
Article
ISSN
0013-4686

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✦ Synopsis

The electrochemical behaviour of diphenyldiselenide in acetonitrile solution was studied by several electrochemical techniques. Controlled potential electrolysis in the presence of cyclohexene was also studied. The cyclic sweep voltammogram exhibited two irreversible anodic peaks at 1.35 and 1.65 V and one cathodic peak at -1.25 V. It was concluded that the primary step is one-electron removal from the substrate, and the Se-Se bond cleavage follows to generate phenylselenium cation and phenylselenium radical, ofwhich the former species can react with cyclohexene to give mainly 2-acetamido-l-phenylselenosyclohexane. The possibility of utilizing phenylselenenic acid as the current mediator in the allylic hydroxylation reaction seems very limited. The cathodic reaction of diphenyldiselenide was also discussed briefly.

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