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Communication | Regular issue | Vol 19, No. 11, 1982, pp.2047-2051
Published online, 1st January, 1970
DOI: 10.3987/R-1982-11-2047
Oxygen-bridged Thia[15]annulenes: Demonstration of a Strong Paramagnetic Ring Current in a 4nπ-Thia-annulene (n=4)

Haru Ogawa, Taiji Imoto, Izumi Miyamoto, Yoichi Taniguchi, Toshitaka Koga, and Yasuyoshi Nogami

*Faculty of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan


The synthesis of 4,7:10,13-diepoxy-2-trans-8,14-di-cis-thia[15]annulene (9) and 4,7:10,13-diepoxy-2,8,14-tri-cis-thia[15]annulene (10) is described. The 1H-nmr spectrum of (9) revealed the existence of a paramagnetic ring current, showing that (9) has a planar and diminished bond alternate rigid frame, as expected for an anti-aromatic 16π system. Conversely, the 1H-nmr spectrum of (10) revealed that (10) is atropic and consequently non-planar.