Oxidative cleavage of diselenide by m-nitrobenzenesulfonyl peroxide. Novel method for the electrophilic benzeneselenenylations of olefins and aromatic rings.
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概要
- 論文の詳細を見る
Diphenyl diselenide was found to be readily converted into benzeneselenenyl <I>m</I>-nitrobenzenesulfonate (PhSeOSO<SUB>2</SUB>C<SUB>6</SUB>H<SUB>4</SUB>NO<SUB>2</SUB>-<I>m</I>) by treating with <I>m</I>-nitrobenzenesulfonyl peroxide. When the selenenyl sulfonate thus formed was allowed to react in situ with olefins, such as cyclohexene, 1-octene, or styrene, in the presence of various nucleophiles, the adducts of benzeneselenenyl group and a nucleophile were obtained. As the nucleophiles water, methanol, acetic acid, phenol, and anisole could be employed; oxyselenenylated ((<U>Remark: Graphics omitted.</U>) : R=H, Me, Ac, and Ph) and arylselenenylated ((<U>Remark: Graphics omitted.</U>) : R=H and Me) adducts were afforded. Phenol gave oxyselenenylated products in cyclohexene or 1-octene and arylselenenylated products in styrene. Efficient intramolecular cyclizations of unsaturated alcohols and carboxylic acids were similarly performed by the selenenyl sulfonate to afford corresponding benzeneselenenylated cyclic ethers and lactones. The selenenyl sulfonate was also found to be a highly reactive benzeneselenenylating reagent for aromatic rings, such as anisole, phenol, acetanilide, toluene, and benzene.
- 公益社団法人 日本化学会の論文
著者
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Yoshida Masato
Department Of Cardiovascular Surgery Hyogo Brain And Heart Center At Himeji
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Kamigata Nobumasa
Department Of Chemistry Faculty Of Science Tokyo Metropolitan University
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Kawamura Kyoko
Department Of Cell Pathology Graduate School Of Medical Sciences Kumamoto University
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Suzuki Takashi
Department Of Anatomic Pathology Tohoku University School Of Medicine
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Kawamura Kyoko
Department of Chemistry, Faculty of Science, Tokyo Metropolitan University
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Sasage Shuichi
Department of Chemistry, Faculty of Science, Tokyo Metropolitan University
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