Synthesis of Frechét-Type Resorcarene Tetrabenzoxazine Dendrimers

Synthesis

Volumn , Issue 2, 2004, Pages 255-262

  Luostarinen, Minna ^a   Laitinen, Teija ^a   Schalley, Christoph A ^b   Rissanen, Kari ^a  

^a UNIVERSITY OF JYVÄSKYLÄ   (Finland)

^b UNIVERSITY OF BONN   (Germany)

Author keywords

Benzoxazines; Dendrimers; ESI TOF mass spectrometry; Mannich bases; Resorcarenes; Supramolecular chemistry

Indexed keywords

AMINES; DENDRIMERS; SYNTHESIS (CHEMICAL);

DENDRITIC WEDGES;

BENZENE;

DENDRIMER; TETRABENAZINE;

ARTICLE; CHEMICAL ANALYSIS; MANNICH REACTION; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS;

EID: 1242296052     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-44361     Document Type: Article

References (38)

1. (a) Tunstad, L. M.; Tucker, J. A.; Dalcanale, E.; Weiser, J.; Bryant, J. A.; Sherman, J. C.; Helgeson, R. C.; Knobler, C. B.; Cram, D. J. J. Org. Chem. 1989, 54, 1305.
2. (b) Timmermann, P.; Verboom, W.; Reinhoudt, D. N. Tetrahedron 1996, 52, 2662.
3. (a) Cram, D. J.; Karbach, S.; Kim, H.-E.; Knobler, C. B.; Maverick, E. F.; Ericson, J. L.; Helgeson, R. C. J. Am. Chem. Soc. 1988, 110, 2229.
4. (b) Tucker, J. A.; Knobler, C. B.; Trueblood, K. N.; Cram, D. J. J. Am. Chem. Soc. 1989, 111, 3688.
5. (c) Moran, J. R.; Ericson, J. L.; Dalcanale, E.; Bryant, J. A.; Knobler, C. B.; Cram, D. J. J. Am. Chem. Soc. 1991, 113, 5707.
6. (d) Cram, D. J.; Tunstad, L. M.; Knobler, C. B. J. Org. Chem. 1992, 57, 528.
7. Cram, D. J.; Choi, H.-J.; Bryant, J. A.; Knobler, C. B. J. Am. Chem. Soc. 1992, 114, 7748.
8. Sherman, J. C.; Knobler, C. B.; Cram, D. J. J. Am. Chem. Soc. 1991, 113, 2194.
9. (a) Cram, D. J.; Tanner, M. E.; Knobler, C. B. J. Am. Chem. Soc. 1991, 113, 7717.
10. (b) Cram, D. J.; Blanda, M. T.; Paek, K.; Knobler, C. B. J. Am. Chem. Soc. 1992, 114, 7765.
11. (c) Cram, D. J.; Jaeger, R.; Deshayes, K. J. Am. Chem. Soc. 1993, 115, 10111.
12. (d) Robbins, T. A.; Knobler, C. B.; Bellew, D. R.; Cram, D. J. J. Am. Chem. Soc. 1994, 116, 111.
13. Timmermann, P.; Verboom, W.; van Veggel, F. C. J. M.; van Hoorn, W. P.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 1292.
14. Grayson, S. M.; Frechét, J. M. J. Chem. Rev. 2001, 101, 3819.
15. (a) Tomalia, D. A.; Baker, H.; Dewald, J.; Hall, M.; Kallos, G.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Polym. J. 1985, 17, 117.
16. (b) Newkome, G. R.; Yao, Z.-Q.; Barker, G. R.; Gupta, V. K. J. Org. Chem. 1985, 50, 2003.
17. (c) Tomalia, D. A.; Naylor, A. M.; Goddard, W. A. III. Angew. Chem., Int. Ed. Engl. 1990, 29, 138.
18. (a) Hawker, C. J.; Frechét, J. M. J. J. Am. Chem. Soc. 1990, 112, 7638.
19. (b) Hawker, C. J.; Frechét, J. M. J. J. Chem. Soc., Chem. Commun. 1990, 1010.
20. (c) Newkome, G. R.; Moorefeld, C. N.; Vögtle, F. Dendritic Molecules: Concepts, Synthesis, Perspective; VCH: Weinheim, 1996.
21. (a) Ferguson, G.; Gallagher, J.; McKervey, M.; Madigan, E. J. Chem. Soc., Perkin Trans. 1 1996, 599.
22. (b) Newkome, G.; Hu, Y.; Saunders, M.; Fronczek, F. Tetrahedron Lett. 1991, 52, 1133.
23. (a) Yamakawa, Y.; Ueda, M.; Nagahata, R.; Takeuchi, K.; Asai, M. J. Chem. Soc., Perkin Trans. 1 1998, 4135.
24. (b) Haba, O.; Haga, K.; Ueda, M. Chem. Mater. 1999, 11, 427.
25. (a) Arnecke, R.; Böhmer, V.; Paulus, E. F.; Vogt, W. J. Am. Chem. Soc. 1995, 117, 3286.
26. (b) Airola, K.; Böhmer, V.; Paulus, E. F.; Rissanen, K.; Schmidt, C.; Thondorf, I.; Vogt, W. Tetrahedron Lett. 1997, 35, 10709.
27. Vögtle, V.; Pleovoets, M.; Nachtsheim, G.; Wörsdörfer, U. J. Prakt. Chem. 1998, 112, 340.
28. Arnecke, R.; Böhmer, V.; Friebe, S.; Gebaner, S.; Krauss, G. J.; Thondorf, I.; Vogt, W. Tetrahedron Lett. 1995, 35, 6221.
29. For a mass spectrometric study of the purity of dendrimers, see: Hummelen, J. C.; van Dongen, J. L. J.; Meijer, E. W. Chem.-Eur. J. 1997, 3, 1489.
30. For reviews on the mass spectrometry of supramolecular aggregates, see: (a) Schalley, C. A. Int. J. Mass Spectrom. 2000, 194, 11. (b) Schalley, C. A. Mass Spectrom. Rev. 2001, 20, 253.
31. For reviews on the mass spectrometry of supramolecular aggregates, see: (a) Schalley, C. A. Int. J. Mass Spectrom. 2000, 194, 11. (b) Schalley, C. A. Mass Spectrom. Rev. 2001, 20, 253.
32. Vainiotalo, P.; Forro, E.; Fulop, F. ACH - Models Chem. 1998, 135, 653.
33. (a) Schalley, C. A.; Castellano, R. K.; Brody, M. S.; Rudkevich, D. M.; Siuzdak, G.; Rebek, J. Jr. J. Am. Chem Soc. 1999, 121, 4568.
34. (b) Brody, M. S.; Rudkevich, D. M.; Schalley, C. A.; Rebek, J. Jr. Angew. Chem., Int. Ed. 1999, 38, 1640.
35. (c) Lützen, A.; Renslo, A. R.; Schalley, C. A.: O'Leary, B. M.; Rebek, J. Jr. J. Am. Chem. Soc. 1999, 121, 7455.
36. (d) O'Leary, B. M.; Szabo, T.; Svenstrup, N.; Schalley, C. A.; Lützen, A.; Rebek, J. Jr. J. Am. Chem. Soc. 2001, 123, 11519.
37. (e) Mansikkamäki, H.; Nissinen, M.; Schalley, C. A.; Rissanen, K. New J. Chem. 2003, 27, 88.
38. Luostarinen, M.; Shivanyuk, A.; Rissanen, K. Org. Lett. 2001, 26, 4141.