An efficient reagent for synthesis of α,β-unsaturated aldehydes 3-methylthio-2-propenyl p-tolyl sulfone |
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Authors: | Katsuyuki Ogura Teruyuki Iihama Kazumasa Takahashi Hirotada Iida |
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Institution: | Department of Synthetic Chemistry, Faculty of Engineering, Chiba University, Yayoicho 1-33, Chiba 260, Japan |
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Abstract: | Alkylation of 3-methylthio-2-propenyl p-tolyl sulfone (1) with an alkyl halide and a base (NaH or KOH-TOMAC) took place at the position α to the sulfonyl group to give optionally a mono- or dialkylated product (2 or 3), which was converted to β-monosubstituted or β,β-disubstituted α,β-unsaturated aldehyde (6 or 7), respectively, by TiCl4-assisted hydrolysis followed by the removal of p-toluenesulfinic acid. |
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