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Synthesis and Redox Behavior of 1-Azulenyl Sulfides and Efficient Synthesis of 1,1′-Biazulenes

✍ Scribed by Taku Shoji; Junya Higashi; Shunji Ito; Kozo Toyota; Toyonobu Asao; Masafumi Yasunami; Kunihide Fujimori; Noboru Morita

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
261 KB
Volume
2008
Category
Article
ISSN
1434-193X

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✦ Synopsis

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.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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