Synthesis of unsymmetrically branched dendrimeric wedges up to the fourth generation based on 2,3-dihydroxybenzyl alcohol

Journal of Organic Chemistry

Volumn 64, Issue 11, 1999, Pages 3796-3797

  Weintraub, Jacob G ^a   Parquette, Jon R ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 DIHYDROXYBENZYL ALCOHOL; ALCOHOL; DENDRIMER; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROPHILICITY; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033612228     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990438l     Document Type: Article

References (24)

1. Newkome, G. R.; Moorefield, C. N.; Vögue, F. Dendritic Molecules-Concepts-Synthesis-Perspectives; VCH: New York, 1996.
2. For a recent review, see: Matthews, O. W.; Shipway, A. N.; Stoddart, J. F. Prog. Polym. Sci. 1998, 23, 1.
3. (a) Lescanec, R. L.; Muthukumar, M. Macromolecules 1990, 23, 2280.
4. (b) Mansfield, M. L.; Klushin, L. I. Macromolecules 1993, 26, 4262.
5. (c) Meltzer, A. D.; Tirrell, D. A.; Jones, A. A.; Inglefield, P. T.; Hedstrand, D. M.; Tomalia, D. A. Macromolecules 1992, 25, 4541.
6. (d) Murat, M.; Grest, G. S. Macromolecules 1996, 29, 1278.
7. (a) Karakaya, B.; Claussen, W.; Gessler, K.; Saenger, W.; Schlüter, A.-D. J. Am. Chem. Soc. 1997, 119, 3296.
8. (b) Wooley, K. L.; Klug, C. A.; Tasaki, K.; Schaefer, J. J. Am. Chem. Soc. 1997, 119, 53.
9. (c) Scherrenberg, R.; Coussens, B.; van Vliet, P.; Edouard, G.; Brackman, J.; de Brabander, E. Macromolecules 1998, 31, 456.
10. (a) Kremers, J. A.; Meijer, E. W. J. Org. Chem. 1994, 59, 4262.
11. (b) Peerlings, H. W. I.; Strunk, M. P.; Meijer, E. W. Chirality 1998, 10, 46.
12. Peerlings, H. W. I.; Trimbach, D. C.; Meijer, E. W. Chem. Commun. 1998, 497.
13. For some recent reviews, see: (a) Peerlings, H. W. I.; Meijer, E. W. Chem. Eur. J. 1997, 3, 1563.
14. (b) Thomas, C. W.; Tor, Y. Chirality 1998, 10, 53.
15. (c) Seebach, D.; Rheiner, P, B.; Greiveldinger, G.; Butz, T.; Sellner, H. Top. Curr. Chem. 1998, 197, 125.
16. (a) Chaumette, J.-L.; Laufersweiler, M. J.; Parquette, J. R. J. Org. Chem. 1998, 63, 9399.
17. (b) Rohde, J. M.; Parquette, J. R. Tetrahedron Lett. 1998, 50, 9161.
18. McElhanon, J. R.; McGrath, D. V. J. Am. Chem. Soc. 1998, 120, 1647.
19. For synthesis of 3,5-branched polyether dendrimers, see: (a) Fréchet, J. M. J.; Hawker, C. J.; Wooley, K. L. J. Macromol. Sci., Pure Appl. Chem. 1994, A31(11), 1627. (b) Hawker, C. J.; Wooley, K. L.; Fréchet, J. M. J. J. Chem. Soc., Perkin Trans. 1 1993, 1287.
20. For synthesis of 3,5-branched polyether dendrimers, see: (a) Fréchet, J. M. J.; Hawker, C. J.; Wooley, K. L. J. Macromol. Sci., Pure Appl. Chem. 1994, A31(11), 1627. (b) Hawker, C. J.; Wooley, K. L.; Fréchet, J. M. J. J. Chem. Soc., Perkin Trans. 1 1993, 1287.
21. This is in contrast to dendritic wedges based on 3,5-dihydroxybenzyl alcohol, which exhibit good solubility in THF from generation one to four. (see ref 10b).
22. Molecular weights for 3-5, determined by MALDI-TOF, were consistent with the expected structures (see Supporting Information).
23. 3 implemented on Macromodel 5.0. This afforded a single conformation within 1 kcal/mol of the global energy minimum.
24. For a comparison of the hydrodynamic volumes of 3,5-branched polyaryl ether dendrons with their exact linear analogues, see: Hawker, C. J.; Malmatröm, E. E.; Frank, C. W.; Kampf, J. P. J. Am. Chem. Soc. 1997, 119, 9903.