Reactions between Nucleophiles and Sulfonium Ions Containing Electron-withdrawing Substituents
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概要
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Sulfonium ions containing electron-withdrawing substituents are formed by the reactions between sulfonium ylides and suitable electrophiles. Reactivities of these sulfonium ions (MeR\overset+S–CX(CO<SUB>2</SUB>Me)<SUB>2</SUB>) with nucleophiles (Y<SUP>−</SUP>) are investigated. The products found are those of 1) C-attack (MeSR+YCX(CO<SUB>2</SUB>Me)<SUB>2</SUB>), 2) Me-attack (MeY+RSCX(CO<SUB>2</SUB>Me)<SUB>2</SUB>) and 3) R-attack (RY+MeSCX(CO<SUB>2</SUB>Me)<SUB>2</SUB>). When R is (+)-2-octyl and Y<SUP>−</SUP> is bromide ion, the RY found is (−)-2-octyl bromide with 59% optical purity. The mechanism of these reactions are discussed.
- 公益社団法人 日本化学会の論文
著者
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Matsuyama Haruo
Department Of Applied Chemistry Faculty Of Engineering Muroran Institute Of Technology
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Minato Hiroshi
Department Of Electrical Engineering And Computer Science Tufts University
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KOBAYASHI Michio
Department of Chemistry and Biological Science, College of Science and Engineering, Aoyama Gakuin Un
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