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Communication | Regular issue | Vol 55, No. 9, 2001, pp.1635-1639
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9262
Synthesis and Complexing Properties of Thiacrownophanes

Seiichi Inokuma, Takashi Funaki, Masayuki Tanakajima, Shinji Nabekura, Keigo Isawa, and Jun Nishimura*

*Gunma University, Department of Chemistry, 1-5-1 Tenjin-cho, Kiryu 376-8515, Japan


Novel thiacrownophanes (1) (cis-form) and (2) (trans-form) were prepared by means of intramolecular [2 + 2] photocycloaddition of styrene derivatives. The ratio of 1:2 was significantly dependent on the oxyethylene chain length of the linkage between the two aromatic nuclei of precursors. In a liquid-liquid extraction, thiacrownophanes (1c) possessing three ethereal oxygens showed perfect selectivity with high efficiency toward Ag+ ion. From ESI-MS analysis, 1c was found to form a 1:1 complex with Ag+ ion in MeCN-H2O homogeneous system.