A New Synthesis of 2-Sulfanyl Allylic Alcohols and. ALPHA.-Sulfanyl Ketones from Carbonyl Compounds and 1-Chloroalkyl p-Tolyl Sulfoxides with Carbon-Carbon …

T Satoh, Y Takahashi, Y Shirai, Y Yamada

Index: Satoh, Tsuyoshi; Takahashi, Yoshinori; Shirai, Yuuichi; Yamada, Yukie Chemical and Pharmaceutical Bulletin, 2006 , vol. 54, # 12 p. 1734 - 1738

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Abstract

Reaction of lithium α-sulfinyl carbanions of 1-chloroalkyl p-tolyl sulfoxides with ketones or aldehydes at low temperature gave adducts in almost quantitative yields. Treatment of the adducts derived from ketones with trifluoroacetic anhydride (TFAA) in the presence of NaI in acetone gave α-sulfanyl allylic alcohols in good to quantitative yields. On the other hand, treatment of the adducts derived from aldehydes with TFAA and NaI resulted in the ...