Intramolecular Stereospecific Pummerer Reactions of Aryl (Substitutedmethyl) Sulfoxides Bearing Electron-withdrawing Groups with Acetic Anhydride

T Numata, O Itoh, T Yoshimura, S Oae

文献索引：Numata, Tatsuo; Itoh, Osamu; Yoshimura, Toshiaki; Oae, Shigeru Bulletin of the Chemical Society of Japan, 1983 , vol. 56, # 1 p. 257 - 265

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被引用次数: 45

摘要

The Pummerer reaction of optically active cyanomethyl aryl sulfoxides with acetic anhydride gave the corresponding α-acetoxy sulfides which were induced with a partial asymmetry nearly 30% at α-carbon, while the 18 O-label of the original sulfoxides was retained in more than 85% in the resulting ester, the Pummerer reaction product. Kinetic experiments with cyanomethyl (p-substituted phenyl) sulfoxides and α, α-dideuterated cyanomethyl p-tolyl ...