Synthesis and redox behavior of 1-azulenyl sulfides and efficient synthesis of 1,1′-biazulenes

Taku Shoji, Junya Higashi, Shunji Ito, Kozo Toyota, Toyonobu Asao, Masafumi Yasunami, Kunihide Fujimori, Noboru Morita

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

The reaction of azulenes with several sulfoxides in the presence of acid anhydrides to afford the corresponding 1-azulenylsulfonium and 1,3-azulenediyldisulfonium ions is reported. The subsequent conversion of these ions in high yields into 1-azulenyl methyl and phenyl sulfides and 1,3-bis(methyl- and phenylthio)azulenes through treatment with diethylamine is also described. Reaction of the 1-azulenyl sulfides with MCPBA afforded 1-azulenyl sulfoxides, which were then efficiently transformed into 1,1′-biazulene derivatives under acidic conditions. The redox properties of 1-azulenyl methyl and phenyl sulfides, 1,3-bis(methyl- and phenylthio)azulenes, and 1,1′-biazulene derivatives bearing methylthio or phenylthio substituents on each azulene ring are reported based on the results of cyclic voltammetry experiments.

Original languageEnglish
Pages (from-to)1242-1252
Number of pages11
JournalEuropean Journal of Organic Chemistry
Issue number7
DOIs
Publication statusPublished - 2008 Mar 1

Keywords

  • 1,1′-biazulene
  • Azulene
  • Cyclic voltammetry
  • Electrochemistry
  • Electrophilic substitution

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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