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Synthesis 1992; 1992(5): 495-498
DOI: 10.1055/s-1992-26145
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Alkoxyacetylenes from Alkyl 1,2-Dichlorovinyl Ethers

Achim Löffler* , Gerhard Himbert
  • *Fachbereich Chemie der Universität Kaiserslautern, Postfach 3049, D-6750 Kaiserslautern, Germany
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Publication Date:
17 September 2002 (online)

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Alkyl 1,2-dichlorovinyl ethers 4, prepared from sodium alkoxides 1 and trichloroethylene 2, react in tetrahydrofuran with two equivalents of butyllithium to afford lithium alkoxyacetylides 5. On the one hand, these acetylides react with ketones or dichlorodimethylsilane to yield the hydroxyalkylated, 6 and silylated alkoxyacetylenes 7, respectively. On the other hand, treatment of 5 with anhydrous zinc chloride and coupling of the obtained zinc acetylides 8 with aryliodides in the presence of a palladium(0) catalyst produces the arylated alkoxyacetylenes 9.