Ring Expansion through a 1,3-Acyl Rearrangement. Reactions of Cyclic Sulfonium Ylides with Acetylenic Compounds
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概要
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Ring expansion of cyclic sulfonium ylides with acetylenic compounds was investigated. It was found that a six-membered cyclic sulfonium ylide (I) gave eight-membered ring expansion products (IIIa—e) in high yields under mild conditions on treatment with acetylenic compounds (IIa—e) in dimethyl sulfoxide. In a similar manner, the reactions of five- and seven-membered cyclic sulonium ylides with II afforded ring expansion products (XIa) and (IXa—c). The ring expansion was considered to proceed through an intramolecular 1,3-acylrearrangement. It was found that, when the reaction of I and IIIa was carried out in benzene, an intermediate bicyclic sulfonium betaine (VIIa) was obtained as yellow precipitates. The properties and reactions of VIIa were investigated. It was shown that the ring expansion product IIIa gave cyclooctenone derivatives (XIIIa—c) by the reaction with some nucleophiles. IIIa was found to give diene esters (XIII, R=acyl)and diene ethers (XIII,R=alkyl) upon reaction with acyl and alkyl halides.
- 公益社団法人 日本化学会の論文
著者
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Mukaiyama Teruaki
Laboratory of Organic Chemistry Tokyo Institute of Technology
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Toyoda Minoru
Laboratory of Organic Chemistry, Tokyo Institute of Technology
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Higo Moriaki
Laboratory of Organic Chemistry, Tokyo Institute of Technology
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Sakashita Takeshi
Laboratory of Organic Chemistry, Tokyo Institute of Technology
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