Conversion of 2-sulfinylated 2-alkenoate esters to (2E,4E)-2,4-alkadienoate esters by pyrolysis.
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概要
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Thermal reaction of ethyl (2<I>E</I>)-2-phenylsulfinyl-2-alkenoates (<I>E</I>-<B>2</B>) prepared from aldehydes and ethyl 2-phenylsulfinylacetate have been investigated. Refluxing of <I>E</I>-<B>2</B> or their <I>Z</I>-isomers in xylene resulted in the formation of ethyl (2<I>E</I>,4<I>E</I>)-2,4-alkadienoates accompanied by ethyl (2<I>E</I>)-4-hydroxy-2-alkenoates. Ethyl 2-cycloalkylidene-2-phenylsulfinylacetates were found to be more susceptible to pyrolysis. The enoate esters (<B>2</B>) undergo migration of their carbon-carbon double bond and then [2,3]sigmatropic rearrangement to benzene-sulfenate esters, followed by thermolytic extrusion of a benzenesulfenic acid probably <I>via</I> ethyl (2<I>E</I>)-4-phenyl-sulfinyl-2-alkenoates to afford ethyl (2<I>E</I>,4<I>E</I>)-2,4-alkadienoates.
- 公益社団法人 日本化学会の論文
著者
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Tanikaga Rikuhei
Department Of Bioscience And Biotechnology Faculty Of Science And Engineering Ritsumeikan University
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Kaji Aritsune
Department of Chemistry, Faculty of Science, Kyoto University
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Kaji Aritsune
Department of Chemistry, Faculty of Science, Kyoto University Sakyo-ku
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Nozaki Yoshihito
Department of Chemistry, Faculty of Science, Kyoto University Sakyo-ku
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Nishida Masaharu
Department of Chemistry, Faculty of Science, Kyoto University Sakyo-ku
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Tanikaga Rikuhei
Department of Chemistry, Faculty of Science, Kyoto University Sakyo-ku
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