フラン誘導体の合成化学的研究(第49報) : 有機イオウPhosphoranesと各種の芳香族アルデヒドのWittig反応について

概要

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Wittig reaction was carried out under usual reaction conditions on sulfur-containing complex ylides, α-(para-substituted phenylthio)ethoxycarbonyl-(III), -cyano-(V), -benzoyl-(VII), and-furoylmethylenetriphenylphosphoranes (IX), with 5-nitro-2-furfural (XI). It was found that, of these complex ylides, IIIa-d and Va-d afforded the corresponding vinyl thioethers. With IIIa-d, reaction was carried out on p-nitrobenzaldehyde (XVIII) and 5-nitro-2-thiophenecarboxaldehyde (XXIII), and the corresponding vinyl thioether compounds were obtained. Each of these thioethers was separated into two kinds of stereoisomers, and their steric configuration was determined from their IR and NMR spectra. The vinyl thioethers were oxidized with hydrogen peroxide to the corresponding vinyl sulfones.
公益社団法人日本薬学会の論文
1969-10-25