Octacarbonyldicobalt(0)-catalyzed ring-opening cyanation of tetrahydrofuran derivatives with trimethylsilyl cyanide.
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概要
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Tetrahydrofuran, less strained cyclic ether was effectively cyanated by trimethylsilyl cyanide ((CH<SUB>3</SUB>)<SUB>3</SUB>SiCN) with its ring-opening to give 5-(trimethylsiloxy)pentanenitrile in 82% yield at 120°C for 23 h in the presence of a catalytic amount of Co<SUB>2</SUB>(CO)<SUB>8</SUB>. Several tetrahydrofuran derivatives having methyl and alkoxyl groups also reacted with trimethylsilyl cyanide to give the corresponding 5-siloxy nitriles in 25–88% yields. On using oxiranes or oxetanes, which are more strained cyclic ethers, however, no reaction proceeded under the same conditions. In the present reaction, (CH<SUB>3</SUB>)<SUB>3</SUB>SiCN would firstly coordinate to the cobalt metal center as its isocyanide form to give a cobalt-isocyanide complex, which would be a precursor of active catalyst species in the reaction.
- 公益社団法人 日本化学会の論文
著者
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Watanabe Yoshihisa
Department Of Basic Geriatrics Graduate School Of Medical Science Kyoto Prefectural University Of Medicine
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Okuda Fumio
Department of Hydrocarbon Chemistry, Faculty of Engineering, Kyoto University
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