A new route for the synthesis of amphiphilic and water-soluble ligands: mono- and di-tertiary phosphines having an alkylene sulfate chain

Abstract

Cyclic sulfates react with LiPPh₂ to form a series of new amphiphilic or water-soluble ligands: monotertiary phosphines with one or two alkylene sulfate chains and ditertiary phosphines with one or two hydrophilic tails attached to bridgehead carbon atom; the application of zwitterionic Rh^I complexes (sulfatephos)₂Rh(cod) and (sulfatediphos)Rh(cod) in liquid biphasic catalysis has been demonstrated for the hydroformylation of styrene and oct-1-ene.

References

1. F. Joó and Á. Kathó, J. Mol. Catal. A: Chem., 1997, 116, 3; B. Cornils, W. A. Hermann and R. W. Eckl, J. Mol. Catal. A: Chem., 1997, 116, 27.
2. W. A. Hermann and C. W. Kohlpainter, Angew. Chem., Int. Ed. Engl., 1993, 32, 1524; D. Sinou, P. Kalck and F. Monteil, Advances In Organometallic Chemistry, Academic Press, 1992, vol. 34, p. 219; M. Barton and J. M. Atwood, J. Coord. Chem., 1991, 24, 43; M. J. Russel, Platinum Metals Rev., 1988, 32, 179.
3. B. Fell and G. Papandogianakis, J. Mol. Catal., 1991, 66, 143; H. Ding, B. E. Hanson, T. Bartik and B. Bartik, Organometallics, 1994, 13, 3761; D. J. Bauer, J. Fischer, S. Kuchen, K. P. Langhans, O. Stelzer and N. Werferling, Z. Naturforsch., Teil B, 1994, 49, 1511; T. Okano, N. Harada and J. Kiji, Chem. Lett., 1994, 6, 1057; H. Ding, B. E. Hanson and J. Bakos, Angew. Chem., Int. Ed. Engl., 1995, 34, 1645; E. Valls, J. Suades, B. Donadieu and R. Mathieu, Chem. Commun., 1996, 771.
4. D. S. Breslow and H. Skolnik, Multi-Sulfur and Sulfur and Oxigen Five- and Six- Membered Heterocycles, Part One, Wiley-Interscience, New York, 1966, p. 17; G. W. Fischer and T. Zimmerman, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katritzky and C. W. Rees, Pergamon, Oxford, 1984, vol. 6, p. 681, J. G. Tillet, Phosphorus Sulfur, 1987, 1, 341.
5. Y. Gao and K. B. Sharpless, J. Am. Chem. Soc., 1988, 110, 7538.
6. D. A. Tomalia and J. Falk, J. Heterocycl. Chem., 1972, 9, 891.
7. D. A. Slack, J. Greveling and M. C. Baird, Inorg. Chem., 1979, 18, 3125.