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Synthesis 2011(15): 2454-2458  
DOI: 10.1055/s-0030-1260066
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Economical Approach to the Synthesis of Unsaturated Thiacrown Ethers

Dong-Qing Sun, Jing-Kui Yang*
College of Chemistry and Chemical Engineering, Graduate University of Chinese Academy of Sciences, Beijing, 100049, P. R. of China
Fax: +86(10)88256092; e-Mail: jkyang@gucas.ac.cn;
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Publication History

Received 25 March 2011
Publication Date:
10 June 2011 (online)

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Abstract

The inexpensive starting material, 1,1-dichloroethylene, was used as a substitute for 1,2-dichloroethylene to synthesize unsaturated thiacrown ethers through the reaction of 1,1-dichloroethylene with sodium sulfide in the presence of a 15-crown-5 catalyst. Besides the compounds containing cis-carbon-carbon double bonds, two unsaturated thiacrown ethers each containing one trans-carbon-carbon double bond were also isolated.

Key words

unsaturated thiacrown ether - 1,1-dichloroethylene - economical approach - macrocyclic compounds - hydrogen anion transfer

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