Synthesis and Redox Behavior of 1-Azulenyl Sulfides and Efficient Synthesis of 1,1′-Biazulenes
Synthesis and Redox Behavior of 1-Azulenyl Sulfides and Efficient Synthesis of 1,1′-Biazulenes
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1-薁基硫醚的合成和氧化还原行为以及1,1′-联薁烯的高效合成
DOI：
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发表时间：
2008
期刊：
影响因子：
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通讯作者：
N. Morita
中科院分区：
文献类型：
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作者：
Taku Shoji;J. Higashi;S. Ito;Kozo Toyota;T. Asao;M. Yasunami;K. Fujimori;N. Morita
据报道，甘菊环与几种亚砜在酸酐存在下反应，得到相应的1-薁基锍和1,3-薁二基二锍离子。还描述了随后通过用二乙胺处理将这些离子高产率转化为1-薁基甲基和苯硫醚以及1,3-双(甲基-和苯硫基)薁烯。 1-薁基硫醚与 MCPBA 反应得到 1-薁基亚砜，然后在酸性条件下有效转化为 1,1'-联薁衍生物。根据循环伏安实验的结果，报告了 1-薁基甲基和苯硫醚、1,3-双（甲基和苯硫基）薁烯以及每个薁环上带有甲硫基或苯硫基取代基的 1,1'-联薁衍生物的氧化还原性质。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 德国， 2008）
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)