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Paper | Regular issue | Vol 63, No. 2, 2004, pp.333-346
Published online, 15th December, 2003
DOI: 10.3987/COM-03-9955
Synthesis and Complexing Properties of Crownophanes Possessing Carboxyl Group

Seiichi Inokuma, Takashi Funaki, Daisuke Hara, and Jun Nishimura*

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


A new series of crown compounds bearing two carboxyl groups (2a-c; crownophanedicarboxylic acids) were prepared via intramolecular [2 + 2] photocycloaddition of bis-styrene derivatives. In the liquid-liquid extraction, crownophanedicarboxylic acids (2a-c) showed a low affinity toward alkali metal cations, though both 2b and 2c showed an extraordinary high affinity toward zinc cation among heavy metal cations examined.