Sulfoxonium ylide chemistry. VIII. A novel rearrangement of dimethylsulfoxonium ylides.

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概要

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• Reduction of dimethylsulfoxonium 3-ethoxycarbonyl-1-[1,2-bis(methoxycarbonyl)vinyl]-2-phenylallylide (<B>1</B>) and dimethylsulfoxonium 3-ethoxycarbonyl-1-[2-(ethoxycarbonyl)vinyl]-2-phenylallylide (<B>5</B>) with zinc in acetic acid gave (<I>Z</I>)- and (<I>E</I>)-3-methoxycarbonyl-4-ethoxycarbonyl-5-phenyl-3,5-hexadienoic acid methyl ester (<B>6a</B> and <B>6b</B>), and (<I>Z</I>)- and (<I>E</I>)-4-ethoxycarbonyl-5-phenyl-3,5-hexadienoic acid ethyl ester (<B>7a</B> and <B>7b</B>), respectively, whose structures were determined by the NMR spectral data and further chemical transformations. The reaction mechanism of the reductive rearrangement was proposed to proceed through an anion radical to form a four membered intermediate (<B>11</B>), which cleaved to non-conjugated dienes leading to <I>Z</I> and <I>E</I> conjugated products.

• 公益社団法人 日本化学会の論文

著者

• IDE Junya

  Central Research Laboratories, Sankyo Co.

• Hiraoka Tetsuo

  Central Research Laboratories, Sankyo Co., Ltd.

• Kishida Yukichi

  Central Research Laboratories, Sankyo Co., Ltd.

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• Sulfoxonium ylide chemistry. VIII. A novel rearrangement of dimethylsulfoxonium ylides.

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