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6930049 
Journal Article 
Synthesis and redox behavior of 1-azulenyl sulfides and efficient synthesis of 1,1'-biazulenes 
Shoji, T; Higashi, J; Ito, S; Toyota, K; Asao, T; Yasunami, M; Fujimori, K; Morita, N; , 
2008 
Yes 
European Journal of Organic Chemistry
ISSN: 1434-193X
EISSN: 1099-0690 
WILEY-V C H VERLAG GMBH 
WEINHEIM 
1242-1252 
WOS:000253919900012 
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.