Anodic oxidation of diphenyl disulfides for preparation of oligo(p-phenylene sulfide)s in acidic media

Kimihisa Yamamoto, Hiroyuki Nishide, Hiroyuki Nishide, Shu Yoshida, Y. S. Park

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Diphenyl disulfides yield oligo(p-phenylene sulfides) by an anodic oxidation in dichloromethane solution in the presence of protonic acids as trifluoroacetic acid. The acid suppresses the nucleophilic reaction of the cationic active species and the electro-oligomerization of diphenyl disulfide proceeds through an electrophilic reaction of a cation formed anodic oxidation. The oxidation of diphenyl disulfide proceeds through a one-electron transfer and via phenylbis(phenylthio) sulfonium cation as an active species in this oligomerization, which was confirmed electrochemically. Upon adding benzoquinones and cerium acetylacetonate to the mixture, the oligomerization proceeds efficiently to give a high yield of the oligomer and can be carried out at a lower applied potential (1.7 to 0.8 V vs. Ag/AgCl).

Original languageEnglish
Pages (from-to)2401-2406
Number of pages6
JournalJournal of the Electrochemical Society
Volume139
Issue number9
Publication statusPublished - 1992 Sep

Fingerprint

Oligomerization
Anodic oxidation
disulfides
Sulfides
sulfides
preparation
oxidation
acids
Cations
Benzoquinones
Positive ions
Cerium
Trifluoroacetic acid
cations
Trifluoroacetic Acid
Acids
Methylene Chloride
Dichloromethane
quinones
cerium

ASJC Scopus subject areas

  • Electrochemistry
  • Surfaces, Coatings and Films
  • Surfaces and Interfaces

Cite this

Anodic oxidation of diphenyl disulfides for preparation of oligo(p-phenylene sulfide)s in acidic media. / Yamamoto, Kimihisa; Nishide, Hiroyuki; Nishide, Hiroyuki; Yoshida, Shu; Park, Y. S.

In: Journal of the Electrochemical Society, Vol. 139, No. 9, 09.1992, p. 2401-2406.

Research output: Contribution to journalArticle

Yamamoto, Kimihisa ; Nishide, Hiroyuki ; Nishide, Hiroyuki ; Yoshida, Shu ; Park, Y. S. / Anodic oxidation of diphenyl disulfides for preparation of oligo(p-phenylene sulfide)s in acidic media. In: Journal of the Electrochemical Society. 1992 ; Vol. 139, No. 9. pp. 2401-2406.
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AU - Park, Y. S.

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AB - Diphenyl disulfides yield oligo(p-phenylene sulfides) by an anodic oxidation in dichloromethane solution in the presence of protonic acids as trifluoroacetic acid. The acid suppresses the nucleophilic reaction of the cationic active species and the electro-oligomerization of diphenyl disulfide proceeds through an electrophilic reaction of a cation formed anodic oxidation. The oxidation of diphenyl disulfide proceeds through a one-electron transfer and via phenylbis(phenylthio) sulfonium cation as an active species in this oligomerization, which was confirmed electrochemically. Upon adding benzoquinones and cerium acetylacetonate to the mixture, the oligomerization proceeds efficiently to give a high yield of the oligomer and can be carried out at a lower applied potential (1.7 to 0.8 V vs. Ag/AgCl).

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