Phosphorus-containing dendrimers. Easy access to new multi-difunctionalized macromolecules

Journal of Organic Chemistry

Volumn 61, Issue 11, 1996, Pages 3799-3805

  Launay, Nathalie ^a   Slany, Michael ^a   Caminade, Anne Marie ^a   Majoral, Jean Pierre ^a  

^a LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000099276     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960045b     Document Type: Article

References (30)

1. Reviews: (a) Tomalia, D. A.; Naylor, A. M.; Goddart, W. A., III. Angew. Chem., Int. Ed. Engl. 1990, 29, 138. (b) Mekelburger, H. B.; Jaworek, W.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1992, 31, 1571. (c) Tomalia, D. A.; Durst, H. D. in Topics in Current Chemistry, vol. 165; Supramolecular Chemistry 1: Directed Synthesis and Molecular Recognition; Weber, E., Ed.; Springer Verlag: Berlin, Heidelberg, 1993; pp 193-313. (d) Ottaviani, M. F.; Bossmann, S.; Turro, N. J.; Tomalia, D. A. J. Am. Chem. Soc. 1994, 116, 661. (e) Fréchet, J. M. J. Science 1994, 263, 1710. (f) Issberner, J.; Moors, R.; Vögtle, F. Angew. Chem. 1994, 106, 2507; Angew. Chem. Int. Ed. Engl. 1994, 33, 2413. (g) Moorefield, C. N.; Newkome, G. R. In Advances in Dendritic Molecules; Newkome, G. R., Ed.; JAI Press: Greenwich CT, 1994; Vol. 1, p 1.
2. Reviews: (a) Tomalia, D. A.; Naylor, A. M.; Goddart, W. A., III. Angew. Chem., Int. Ed. Engl. 1990, 29, 138. (b) Mekelburger, H. B.; Jaworek, W.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1992, 31, 1571. (c) Tomalia, D. A.; Durst, H. D. in Topics in Current Chemistry, vol. 165; Supramolecular Chemistry 1: Directed Synthesis and Molecular Recognition; Weber, E., Ed.; Springer Verlag: Berlin, Heidelberg, 1993; pp 193-313. (d) Ottaviani, M. F.; Bossmann, S.; Turro, N. J.; Tomalia, D. A. J. Am. Chem. Soc. 1994, 116, 661. (e) Fréchet, J. M. J. Science 1994, 263, 1710. (f) Issberner, J.; Moors, R.; Vögtle, F. Angew. Chem. 1994, 106, 2507; Angew. Chem. Int. Ed. Engl. 1994, 33, 2413. (g) Moorefield, C. N.; Newkome, G. R. In Advances in Dendritic Molecules; Newkome, G. R., Ed.; JAI Press: Greenwich CT, 1994; Vol. 1, p 1.
3. Reviews: (a) Tomalia, D. A.; Naylor, A. M.; Goddart, W. A., III. Angew. Chem., Int. Ed. Engl. 1990, 29, 138. (b) Mekelburger, H. B.; Jaworek, W.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1992, 31, 1571. (c) Tomalia, D. A.; Durst, H. D. in Topics in Current Chemistry, vol. 165; Supramolecular Chemistry 1: Directed Synthesis and Molecular Recognition; Weber, E., Ed.; Springer Verlag: Berlin, Heidelberg, 1993; pp 193-313. (d) Ottaviani, M. F.; Bossmann, S.; Turro, N. J.; Tomalia, D. A. J. Am. Chem. Soc. 1994, 116, 661. (e) Fréchet, J. M. J. Science 1994, 263, 1710. (f) Issberner, J.; Moors, R.; Vögtle, F. Angew. Chem. 1994, 106, 2507; Angew. Chem. Int. Ed. Engl. 1994, 33, 2413. (g) Moorefield, C. N.; Newkome, G. R. In Advances in Dendritic Molecules; Newkome, G. R., Ed.; JAI Press: Greenwich CT, 1994; Vol. 1, p 1.
4. Reviews: (a) Tomalia, D. A.; Naylor, A. M.; Goddart, W. A., III. Angew. Chem., Int. Ed. Engl. 1990, 29, 138. (b) Mekelburger, H. B.; Jaworek, W.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1992, 31, 1571. (c) Tomalia, D. A.; Durst, H. D. in Topics in Current Chemistry, vol. 165; Supramolecular Chemistry 1: Directed Synthesis and Molecular Recognition; Weber, E., Ed.; Springer Verlag: Berlin, Heidelberg, 1993; pp 193-313. (d) Ottaviani, M. F.; Bossmann, S.; Turro, N. J.; Tomalia, D. A. J. Am. Chem. Soc. 1994, 116, 661. (e) Fréchet, J. M. J. Science 1994, 263, 1710. (f) Issberner, J.; Moors, R.; Vögtle, F. Angew. Chem. 1994, 106, 2507; Angew. Chem. Int. Ed. Engl. 1994, 33, 2413. (g) Moorefield, C. N.; Newkome, G. R. In Advances in Dendritic Molecules; Newkome, G. R., Ed.; JAI Press: Greenwich CT, 1994; Vol. 1, p 1.
5. Reviews: (a) Tomalia, D. A.; Naylor, A. M.; Goddart, W. A., III. Angew. Chem., Int. Ed. Engl. 1990, 29, 138. (b) Mekelburger, H. B.; Jaworek, W.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1992, 31, 1571. (c) Tomalia, D. A.; Durst, H. D. in Topics in Current Chemistry, vol. 165; Supramolecular Chemistry 1: Directed Synthesis and Molecular Recognition; Weber, E., Ed.; Springer Verlag: Berlin, Heidelberg, 1993; pp 193-313. (d) Ottaviani, M. F.; Bossmann, S.; Turro, N. J.; Tomalia, D. A. J. Am. Chem. Soc. 1994, 116, 661. (e) Fréchet, J. M. J. Science 1994, 263, 1710. (f) Issberner, J.; Moors, R.; Vögtle, F. Angew. Chem. 1994, 106, 2507; Angew. Chem. Int. Ed. Engl. 1994, 33, 2413. (g) Moorefield, C. N.; Newkome, G. R. In Advances in Dendritic Molecules; Newkome, G. R., Ed.; JAI Press: Greenwich CT, 1994; Vol. 1, p 1.
6. Reviews: (a) Tomalia, D. A.; Naylor, A. M.; Goddart, W. A., III. Angew. Chem., Int. Ed. Engl. 1990, 29, 138. (b) Mekelburger, H. B.; Jaworek, W.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1992, 31, 1571. (c) Tomalia, D. A.; Durst, H. D. in Topics in Current Chemistry, vol. 165; Supramolecular Chemistry 1: Directed Synthesis and Molecular Recognition; Weber, E., Ed.; Springer Verlag: Berlin, Heidelberg, 1993; pp 193-313. (d) Ottaviani, M. F.; Bossmann, S.; Turro, N. J.; Tomalia, D. A. J. Am. Chem. Soc. 1994, 116, 661. (e) Fréchet, J. M. J. Science 1994, 263, 1710. (f) Issberner, J.; Moors, R.; Vögtle, F. Angew. Chem. 1994, 106, 2507; Angew. Chem. Int. Ed. Engl. 1994, 33, 2413. (g) Moorefield, C. N.; Newkome, G. R. In Advances in Dendritic Molecules; Newkome, G. R., Ed.; JAI Press: Greenwich CT, 1994; Vol. 1, p 1.
7. Reviews: (a) Tomalia, D. A.; Naylor, A. M.; Goddart, W. A., III. Angew. Chem., Int. Ed. Engl. 1990, 29, 138. (b) Mekelburger, H. B.; Jaworek, W.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1992, 31, 1571. (c) Tomalia, D. A.; Durst, H. D. in Topics in Current Chemistry, vol. 165; Supramolecular Chemistry 1: Directed Synthesis and Molecular Recognition; Weber, E., Ed.; Springer Verlag: Berlin, Heidelberg, 1993; pp 193-313. (d) Ottaviani, M. F.; Bossmann, S.; Turro, N. J.; Tomalia, D. A. J. Am. Chem. Soc. 1994, 116, 661. (e) Fréchet, J. M. J. Science 1994, 263, 1710. (f) Issberner, J.; Moors, R.; Vögtle, F. Angew. Chem. 1994, 106, 2507; Angew. Chem. Int. Ed. Engl. 1994, 33, 2413. (g) Moorefield, C. N.; Newkome, G. R. In Advances in Dendritic Molecules; Newkome, G. R., Ed.; JAI Press: Greenwich CT, 1994; Vol. 1, p 1.
8. Reviews: (a) Tomalia, D. A.; Naylor, A. M.; Goddart, W. A., III. Angew. Chem., Int. Ed. Engl. 1990, 29, 138. (b) Mekelburger, H. B.; Jaworek, W.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1992, 31, 1571. (c) Tomalia, D. A.; Durst, H. D. in Topics in Current Chemistry, vol. 165; Supramolecular Chemistry 1: Directed Synthesis and Molecular Recognition; Weber, E., Ed.; Springer Verlag: Berlin, Heidelberg, 1993; pp 193-313. (d) Ottaviani, M. F.; Bossmann, S.; Turro, N. J.; Tomalia, D. A. J. Am. Chem. Soc. 1994, 116, 661. (e) Fréchet, J. M. J. Science 1994, 263, 1710. (f) Issberner, J.; Moors, R.; Vögtle, F. Angew. Chem. 1994, 106, 2507; Angew. Chem. Int. Ed. Engl. 1994, 33, 2413. (g) Moorefield, C. N.; Newkome, G. R. In Advances in Dendritic Molecules; Newkome, G. R., Ed.; JAI Press: Greenwich CT, 1994; Vol. 1, p 1.
9. See for example (a) Jansen, J. F. G. A.; De Brabander van der Berg, E. M. M.; Meijer, E. W. Science 1994, 32, 1226. (b) Lee, J. J.; Ford, W. T.; Moore, J. A.; Li, Y. F. Macromolecules 1994, 27, 4632. (c) Van der Made, A. W.; Van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1992, 1400. (d) Knapen, J. W. J.; Van der Made, A. W.; De Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659.
10. See for example (a) Jansen, J. F. G. A.; De Brabander van der Berg, E. M. M.; Meijer, E. W. Science 1994, 32, 1226. (b) Lee, J. J.; Ford, W. T.; Moore, J. A.; Li, Y. F. Macromolecules 1994, 27, 4632. (c) Van der Made, A. W.; Van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1992, 1400. (d) Knapen, J. W. J.; Van der Made, A. W.; De Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659.
11. See for example (a) Jansen, J. F. G. A.; De Brabander van der Berg, E. M. M.; Meijer, E. W. Science 1994, 32, 1226. (b) Lee, J. J.; Ford, W. T.; Moore, J. A.; Li, Y. F. Macromolecules 1994, 27, 4632. (c) Van der Made, A. W.; Van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1992, 1400. (d) Knapen, J. W. J.; Van der Made, A. W.; De Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659.
12. See for example (a) Jansen, J. F. G. A.; De Brabander van der Berg, E. M. M.; Meijer, E. W. Science 1994, 32, 1226. (b) Lee, J. J.; Ford, W. T.; Moore, J. A.; Li, Y. F. Macromolecules 1994, 27, 4632. (c) Van der Made, A. W.; Van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1992, 1400. (d) Knapen, J. W. J.; Van der Made, A. W.; De Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659.
13. (a) Launay, N.; Caminade, A.-M.; Lahana, R.; Majoral, J.-P. Angew. Chem., Int. Ed. Engl. 1994, 33, 1589.
14. (b) Launay, N.; Caminade, A.-M.; Majoral, J.-P. J. Am. Chem. Soc. 1995, 117, 3282.
15. (c) Galliot, C.; Prévoté, D.; Caminade, A.-M.; Majoral, J.-P. J. Am. Chem. Soc. 1995, 117, 5470.
16. (d) Slany, M.; Bardaji, M.; Casanove, M. J.; Caminade, A.-M.; Majoral, J.-P.; Chaudret, D. J. Am. Chem. Soc. 1995, 117, 9764.
17. See for example: (a) Tomalia, D. A.; Baker, H.; Dewald, H.; Hall, M.; Kallos, C.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Polymer J. 1985, 17, 117. (b) Tomalia, D. A.; Baker, H.; Dewald, J.; Hall, M.; Kallos, C.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Macromolecules 1986, 19, 2466. (c) Meltzer, A. D.; Tinell, D. A.; Jones, A. A.; Inglefield, D.; Hedstrand, M.; Tomalia, D. A. Macromolecules 1992, 25, 4541. (d) Tomalia, D. A. Top. Curr. Chem. 1993, 165, 193. (e) Hawker, C. J.; Fréchet, J. M. J. Macromolecules 1990, 23, 4726. (f) Wooley, K. L.; Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1993, 115, 11496. (g) Hawker, C. J.; Wooley, K. L.; Fréchet, J. M. J. J. Chem. Soc. Perkin Trans 1 1993, 1287.
18. See for example: (a) Tomalia, D. A.; Baker, H.; Dewald, H.; Hall, M.; Kallos, C.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Polymer J. 1985, 17, 117. (b) Tomalia, D. A.; Baker, H.; Dewald, J.; Hall, M.; Kallos, C.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Macromolecules 1986, 19, 2466. (c) Meltzer, A. D.; Tinell, D. A.; Jones, A. A.; Inglefield, D.; Hedstrand, M.; Tomalia, D. A. Macromolecules 1992, 25, 4541. (d) Tomalia, D. A. Top. Curr. Chem. 1993, 165, 193. (e) Hawker, C. J.; Fréchet, J. M. J. Macromolecules 1990, 23, 4726. (f) Wooley, K. L.; Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1993, 115, 11496. (g) Hawker, C. J.; Wooley, K. L.; Fréchet, J. M. J. J. Chem. Soc. Perkin Trans 1 1993, 1287.
19. See for example: (a) Tomalia, D. A.; Baker, H.; Dewald, H.; Hall, M.; Kallos, C.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Polymer J. 1985, 17, 117. (b) Tomalia, D. A.; Baker, H.; Dewald, J.; Hall, M.; Kallos, C.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Macromolecules 1986, 19, 2466. (c) Meltzer, A. D.; Tinell, D. A.; Jones, A. A.; Inglefield, D.; Hedstrand, M.; Tomalia, D. A. Macromolecules 1992, 25, 4541. (d) Tomalia, D. A. Top. Curr. Chem. 1993, 165, 193. (e) Hawker, C. J.; Fréchet, J. M. J. Macromolecules 1990, 23, 4726. (f) Wooley, K. L.; Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1993, 115, 11496. (g) Hawker, C. J.; Wooley, K. L.; Fréchet, J. M. J. J. Chem. Soc. Perkin Trans 1 1993, 1287.
20. See for example: (a) Tomalia, D. A.; Baker, H.; Dewald, H.; Hall, M.; Kallos, C.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Polymer J. 1985, 17, 117. (b) Tomalia, D. A.; Baker, H.; Dewald, J.; Hall, M.; Kallos, C.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Macromolecules 1986, 19, 2466. (c) Meltzer, A. D.; Tinell, D. A.; Jones, A. A.; Inglefield, D.; Hedstrand, M.; Tomalia, D. A. Macromolecules 1992, 25, 4541. (d) Tomalia, D. A. Top. Curr. Chem. 1993, 165, 193. (e) Hawker, C. J.; Fréchet, J. M. J. Macromolecules 1990, 23, 4726. (f) Wooley, K. L.; Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1993, 115, 11496. (g) Hawker, C. J.; Wooley, K. L.; Fréchet, J. M. J. J. Chem. Soc. Perkin Trans 1 1993, 1287.
21. See for example: (a) Tomalia, D. A.; Baker, H.; Dewald, H.; Hall, M.; Kallos, C.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Polymer J. 1985, 17, 117. (b) Tomalia, D. A.; Baker, H.; Dewald, J.; Hall, M.; Kallos, C.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Macromolecules 1986, 19, 2466. (c) Meltzer, A. D.; Tinell, D. A.; Jones, A. A.; Inglefield, D.; Hedstrand, M.; Tomalia, D. A. Macromolecules 1992, 25, 4541. (d) Tomalia, D. A. Top. Curr. Chem. 1993, 165, 193. (e) Hawker, C. J.; Fréchet, J. M. J. Macromolecules 1990, 23, 4726. (f) Wooley, K. L.; Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1993, 115, 11496. (g) Hawker, C. J.; Wooley, K. L.; Fréchet, J. M. J. J. Chem. Soc. Perkin Trans 1 1993, 1287.
22. See for example: (a) Tomalia, D. A.; Baker, H.; Dewald, H.; Hall, M.; Kallos, C.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Polymer J. 1985, 17, 117. (b) Tomalia, D. A.; Baker, H.; Dewald, J.; Hall, M.; Kallos, C.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Macromolecules 1986, 19, 2466. (c) Meltzer, A. D.; Tinell, D. A.; Jones, A. A.; Inglefield, D.; Hedstrand, M.; Tomalia, D. A. Macromolecules 1992, 25, 4541. (d) Tomalia, D. A. Top. Curr. Chem. 1993, 165, 193. (e) Hawker, C. J.; Fréchet, J. M. J. Macromolecules 1990, 23, 4726. (f) Wooley, K. L.; Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1993, 115, 11496. (g) Hawker, C. J.; Wooley, K. L.; Fréchet, J. M. J. J. Chem. Soc. Perkin Trans 1 1993, 1287.
23. See for example: (a) Tomalia, D. A.; Baker, H.; Dewald, H.; Hall, M.; Kallos, C.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Polymer J. 1985, 17, 117. (b) Tomalia, D. A.; Baker, H.; Dewald, J.; Hall, M.; Kallos, C.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Macromolecules 1986, 19, 2466. (c) Meltzer, A. D.; Tinell, D. A.; Jones, A. A.; Inglefield, D.; Hedstrand, M.; Tomalia, D. A. Macromolecules 1992, 25, 4541. (d) Tomalia, D. A. Top. Curr. Chem. 1993, 165, 193. (e) Hawker, C. J.; Fréchet, J. M. J. Macromolecules 1990, 23, 4726. (f) Wooley, K. L.; Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1993, 115, 11496. (g) Hawker, C. J.; Wooley, K. L.; Fréchet, J. M. J. J. Chem. Soc. Perkin Trans 1 1993, 1287.
24. (a) Badri, M.; Majoral, J.-P., Caminade, A.-M.; Delmas, M.; Gaset, A.; Gorgues, A.; Jaud, J. J. Am. Chem. Soc. 1990, 112, 5618.
25. (b) Gonce, F.; Caminade, A.-M.; Majoral, J.-P.; Jaud, J., Vignaux, J. Bull. Soc. Chim. Fr. 1992, 129, 237.
26. (c) Oussaid, B.; Garrigues, B.; Jaud, J.; Caminade, A.-M.; Majoral, J.-P. J. Org. Chem. 1993, 58, 4500.
27. (d) Colombo-Khater, D.; He, Z.; Caminade, A.-M.; Dahan, F.; Kraemer, R.; Majoral, J.-P. Synthesis 1993, 1145.
28. (e) Colombo-Khater, D.; Caminade, A.-M.; Raynaud, B.; Jaud, J.; Majoral, J.-P. Bull. Soc. Chim. Fr. 1994, 131, 733.
29. (f) Mitjaville, J.; Caminade, A.-M.; Daran, J.-C.; Donnadieu, B.; Majoral, J.-P. J. Am. Chem. Chem. Soc. 1995, 117, 1712.
30. Fachin, G.; Bertani, R.; Berton, A.; Gleria, M. Inorg. Chim. Acta 1988, 147, 165.