473665-48-4Relevant academic research and scientific papers
Unsaturated thiacrown ethers: Synthesis, physical properties, and formation of a silver complex
Tsuchiya,Shimizu,Kamigata
, p. 11534 - 11538 (2001)
The 6-, 9-, 12-, 15-, 18-, 21-, 24-, and 27-membered unsaturated thiacrown ethers 1-8 were formed by reaction of cis-1,2-dichloroethylene with sodium sulfide in acetonitrile. Crystal structures of 4-8 were determined by X-ray crystallography, and it was found that all sulfur atoms of 5-8 direct to the inside of the ring (endodentate). All of the ORTEP drawings show that there are cavities in these molecules, and the cavity sizes in 4-8 were 1.76, 2.34, 3.48, 4.43, and 5.36 A, respectively. The UV spectra of 4-8 showed absorption maximums at the range of 255-276 nm in acetonitrile, and the absorption maximums of 4-8 were found to shift to longer wavelengths by changing the solvent from acetonitrile to cyclohexane. The cyclic voltammograms of 4-8 indicate that the larger unsaturated thiacrown ethers were oxidized more easily than the smaller systems, and unsaturated thiacrown ethers were oxidized more easily than corresponding saturated systems. The reaction of 4 with silver trifluoroacetate in acetone afforded the colorless complex Ag1(C2H2S)5(CF3COO) 9. The crystal structure of 9 was determined by X-ray analysis, and it was found that three of the five sulfur atoms bonded to the silver atom.
An economical approach to the synthesis of unsaturated thiacrown ethers
Sun, Dong-Qing,Yang, Jing-Kui
experimental part, p. 2454 - 2458 (2011/09/20)
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. Georg Thieme Verlag Stuttgart New York.
