The Synthesis of Sulfo Derivatives of Calix[4]arenes Yury Yu. Morzherin Ekaterinburg Department of Technology for Organic Synthesis The Urals State Technical.

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Presentation transcript:

The Synthesis of Sulfo Derivatives of Calix[4]arenes Yury Yu. Morzherin Ekaterinburg Department of Technology for Organic Synthesis The Urals State Technical University – UPI

Sulfo Derivatives of Calix[4]arenes Shinkai S.; Mori S.; Sone T.; Manade O. Tetrahedron Lett. 1984, 25, 5315 Scharff J.; Mahjoubi M. J.New.Chem. 1991, 15, 883

Water-soluble Receptors S.Shinkai, K.Araki, M. Kubota, T. Arimura, T.Matsuda, J.Org.Chem. 1991, 56, 295 for Cu 2+, Zn 2+, Ni 2+, UO 2 2+ G.Arena, A.Contino, F.Gulino, A.Margi, D.Sciotto, R.Ungaro, Tetrahedron Lett. 2000, 41, 9327 for acetonitrile, acetone

Chlorosulfonylated of Calix[4]arene Morzherin, Yu.; Rudkevich, D.M.; Verboom, W.; Reinhoudt, D.N. J.Org.Chem. 1993, 58, 7602 for R = Me, Et, Pr

The Synthesis of Anion Receptors

Anion Receptors Cl - HSO 4 - HNO 3 - ClO 4 - K ass = <1 Morzherin, Yu.; Rudkevich, D.M.; Verboom, W.; Reinhoudt, D.N. J.Org.Chem. 1993, 58, 7602 Cl - HSO 4 - HNO 3 - ClO 4 - K ass = <1

Synthesis of p-sulfonatocalix[4]arenes

SO 3 (30-40%) H 2 SO 4 Sodium free H 2 SO 4 SO 3 (30-40%) Sodium free

H 2 SO 4 SO 3 (30-40%)

Synthesis of ditopic receptors

The NMR Determination of K ass

K ass, M -1 in CH 3 CN-H 2 O R 1 = i-Pr t-Bu Cl - HSO R 1 = i-Pr t-Bu Cl - HSO

Acknowledgment Prof. David Reinhoudt Dr. Wim Verboom Dr. Dmitry Rudkevich The authors also thank the Russian Foundation for Basic Research (Grant a) Research team A.I. Matern, PhD T.V. Glukhareva, PhD M.F. Kosterina, PhD-student