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Synthesis and Redox Behavior of 1‐Azulenyl Sulfides and Efficient Synthesis of 1,1′‐Biazulenes
Author(s) -
Shoji Taku,
Higashi Junya,
Ito Shunji,
Toyota Kozo,
Asao Toyonobu,
Yasunami Masafumi,
Fujimori Kunihide,
Morita Noboru
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700959
Subject(s) - azulene , chemistry , diethylamine , redox , cyclic voltammetry , medicinal chemistry , ion , organic chemistry , electrochemistry , electrode
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)