A novel consecutive reaction of lithium acetylides with 2-aryl-1-chlorovinyl p-tolyl sulfoxides leading to the formation of (Z)-enediynes

…, Y Nishimura, N Ishida, H Momochi, H Yamashita…

Index: Kimura, Tsutomu; Nishimura, Yuka; Ishida, Naoyuki; Momochi, Hitoshi; Yamashita, Hironori; Satoh, Tsuyoshi Tetrahedron Letters, 2013 , vol. 54, # 9 p. 1049 - 1051

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Citation Number: 4

Abstract

The reaction of (E)-2-aryl-1-chlorovinyl p-tolyl sulfoxides with lithium acetylides gave a variety of (Z)-3-arylhex-3-ene-1, 5-diynes in yields of up to 80% with high stereoselectivity. The structure of the (Z)-enediyne was confirmed by X-ray molecular structure analysis. The result of the reaction with deuterium-and 13C-labeled sulfoxide suggested that the reaction proceeds through cleavage of the C–H bond at the β-position of the 2-aryl-1-chlorovinyl ...

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