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

Autor:	Kozo Toyota, Junya Higashi, Kunihide Fujimori, Toyonobu Asao, Noboru Morita, Shunji Ito, Taku Shoji, Masafumi Yasunami
Rok vydání:	2008
Předmět:	Diethylamine chemistry.chemical_compound Electrophilic substitution chemistry Organic Chemistry Organic chemistry Physical and Theoretical Chemistry Cyclic voltammetry Azulene Electrochemistry Ring (chemistry) Redox Medicinal chemistry
Zdroj:	European Journal of Organic Chemistry. 2008:1242-1252
ISSN:	1099-0690 1434-193X
Popis:	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)
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::65c17c3ebab2cb8bf223a10b712e5a7b https://doi.org/10.1002/ejoc.200700959 Zobrazit plný text záznamu Plný text