Vilsmeier-Haack Reaction of α-Oxo Ketene Dithioacetals to α-Chlorovinyl/Ethynyl Ketene Dithioacetals

Dewen Dong; Yingchun Liu; Yulong Zhao; Yimei Qi; Zhuo Wang; Qun Liu

doi:10.1055/s-2004-834901

PAPER

Vilsmeier-Haack Reaction of α-Oxo Ketene Dithioacetals to α-Chlorovinyl/Ethynyl Ketene Dithioacetals

Dewen Dong*, Yingchun Liu, Yulong Zhao, Yimei Qi, Zhuo Wang, Qun Liu*
Department of Chemistry, Northeast Normal University, Changchun, 130024, P. R. China
Fax: +86(431)5098966; e-Mail: dongdw663@nenu.edu.cn;

Abstract

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Abstract

A range of α-oxo ketene dithioacetals 1 reacted with Vilsmeier reagent (POCl₃/DMF) to afford α-chlorovinyl ketene dithioacetals 2. With the treatment of NaOH in ethanol or methanol, the compounds 2 were transformed into the corresponding α-ethynyl ketene dithioacetals 3 in moderate to high yields.

Key words

alkyne - α-ethynyl ketene dithioacetal - α-chlorovinyl ketene dithioacetal - α-oxo ketene dithioacetal - Vilsmeier-Haack reaction

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References

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