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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 186, 2011 - Issue 5: 24th International Symposium on the Organic Chemistry of Sulfur
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Oral Contributions

Synthesis and Stereochemistry of Thiacrown Ethers with Unsaturated Bonds

Professor Toshio Shimizu Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, Tokyo, Japan
,
Mr. Satoru Komatsuzaki Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, Tokyo, Japan
,
Mr. Junryo Kuwahara Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, Tokyo, Japan
&
Dr. Kazunori Hirabayashi Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, Tokyo, Japan
Pages 1225-1228 | Received 28 Jun 2010, Accepted 22 Sep 2010, Published online: 12 Jul 2011
 
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Abstract

Partially unsaturated 14- and 28-membered thiacrown ethers with Z-olefins were synthesized. The crystal structures of some of the macrocycles were determined by X-ray crystallographic analysis, and the 28-membered thiacrown ethers were found to have slender structures in the crystalline state. The 14-membered thiacrown ether without any substituent was found to be oxidized more easily than the corresponding thiacrown ether possessing hydroxyl groups. Heating of the 14-membered macrocycles was found to cause the Z,E-isomerization reactions to give the corresponding E,Z- and E,E-isomers.

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