Synthesis and helicity of optically active poly(N- propargylphosphonamidates) having chiral phosphorus center

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 45, Issue 8, 2007, Pages 1515-1524

  Yue, Dongmei ^a   Fujii, Toru ^a   Terada, Kayo ^a   Tabei, Junichi ^a   Shiotsuki, Masashi ^a   Sanda, Fumio ^a   Masuda, Toshio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Chiral; Helical conformation; N propargylphosphonamidate; Polyacetylenes; Synthesis

Indexed keywords

CHEMICAL STABILITY; CHIRALITY; HYDROGEN BONDS; MOLECULAR WEIGHT; PHOSPHORUS; SYNTHESIS (CHEMICAL);

HELICAL CONFORMATION; N-PROPARGYLPHOSPHONAMIDATE; PHOSPHONIC DICHLORIDES; PROPARGYLAMINE;

POLYACETYLENES;

EID: 34247326026     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.21922     Document Type: Article

References (50)

1. (a) Watson, J. D.; Crick, F. H. C. Nature 1953, 171, 737;
2. (b) Saenger, W. Principles of Nucleic Acid Structure; Springer-Verlag: New York, 1984;
3. (c) Branden, C.; Tooze, J. Introduction to Protein Structure; Garland: New York, 1991.
4. (a) Green, M. M.; Cheon, K.-S.; Yang, S.-Y.; Park, J.-W.; Swansburg, S.; Liu, W. Acc Chem Res 2001, 34, 672;
5. (b) Nakano, T.; Okamoto, Y. Chem Rev 2001, 101, 4013;
6. (c) Sato, T.; Terao, K.; Teramoto, A.; Fujiki, M. Polymer 2003, 44, 5477;
7. (d) Yashima, E.; Maeda, K.; Nishimura, T. Chem Eur J 2004, 10, 42;
8. (e) Lam, J. W. Y.; Tang, B. Z. Acc Chem Res 2005, 38, 745;
9. (f) Aoki, T.; Kaneko, T. Polym J 2005, 37, 717.
10. (a) Nakako, H.; Nomura, R.; Tabata, M.; Masuda, T. Macromolecules 1999, 32, 2861;
11. (b) Nakako, H.; Mayahara, Y.; Nomura, R.; Tabata, M.; Masuda, T. Macromolecules 2000, 33, 3978;
12. (c) Nomura, R.; Fukushima, Y.; Nakako, H.; Masuda, T. J. Am Chem Soc 2000, 122, 8830;
13. (d) Nakako, H.; Nomura, R.; Masuda, T. Macromolecules 2001, 34, 1496.
14. (a) Nomura, R.; Tabei, J.; Masuda, T. J Am Chem Soc 2001, 123, 8430;
15. (b) Nomura, R.; Tabei, J.; Masuda, T. Macromolecules 2002, 35, 2955;
16. (c) Tabei, J.; Nomura, R.; Masuda, T. Macromolecules 2002, 35, 5405;
17. (d) Nomura, R.; Tabei, J.; Nishiura, S.; Masuda, T. Macromolecules 2003, 36, 561;
18. (e) Nomura, R.; Yamada, K.; Tabei, J.; Takakura, Y.; Takigawa, T.; Masuda, T. Macromolecules 2003, 36, 6939;
19. (f) Tabei, J.; Nomura, R.; Masuda, T. Macromolecules 2003, 36, 573;
20. (g) Tabei, J.; Nomura, R.; Sanda, F.; Masuda, T. Macromolecules 2004, 37, 1175;
21. (h) Tabei, J.; Nomura, R.; Shiotsuki, M.; Sanda, F.; Masuda, T. Macromolecules 2005, 36, 8603;
22. (i) Tabe, J.; Nomura, R.; Sanda, F.; Masuda, T. Macromol Chem Phys 2005, 206, 323;
23. (j) Tabei, J.; Shiotsuki, M.; Sanda, F.; Masuda, T. Macromolecules 2005, 38, 5860;
24. (k) Tabei, J.; Shiotsuki, M.; Sato, T.; Sanda, F.; Masuda, T. Chem Eur J 2005, 11, 3591.
25. (a) Nomura, R.; Nishiura, S.; Tabei, J.; Sanda, F.; Masuda, T. Macromolecules 2003, 36, 5076;
26. (b) Sanda, F.; Nishiura, S.; Shiotsuki, M.; Masuda, T. Macromolecules 2005, 38, 3075.
27. Engel, R. Handbook of Organo-Phosphorus Chemistry; Marcel Decker: New York, 1992.
28. (a) Westheimer, F. H. Science 1987, 235, 1173;
29. (b) Seto, H.; Kuzuyama, T. Nat Prod Rep 1999, 16, 589.
30. (a) Stec, W. J. Organophosphorus Chem 1982, 13, 145;
31. (b) Mader, M. M.; Bartlett, P. A. Chem Rev 1997, 97, 1281.
32. Dubrovina, N. V.; Borner, A. Angew Chem Int Ed 2004, 43, 5883.
33. (a) Motoyoshiya, J. Trends Org Chem 1998, 7, 63;
34. (b) Kann, N.; Rein, T. Synthesis 2003, 579;
35. (c) Bricklebank, N. Organophosphorus Chem 2003, 33, 289.
36. Scott, R.; Rajski, S. R.; Williams, R. M. Chem Rev 1998, 98, 2723.
37. Kafarski, P.; Lejczak, B. Phosphorus Sulfur 1991, 63, 193.
38. Davis, F. A.; Ramachandar, T.; Wu, Y. J Org Chem 2003, 68, 6894.
39. Palacios, F.; Ochoa de Retana, A. M.; Gil, J. I. Tetrahedron Lett 2000, 41, 5363.
40. Palacios, F.; Ochoa de Retana, A. M.; Gil, J. I.; Ezpeleta, J. M. J Org Chem 2000, 65, 3213.
41. (a) Bowyer, P. K.; Cook, V. C.; Gharib-Naseri, N.; Gugger, P. A.; Rae, A. D.; Swiegers, G. F.; Willis, A. C.; Zank, J.; Wild, S. B. Proc Natl Acad Sci USA 2002, 99, 4877;
42. (b) Morisaki, Y.; Ouchi, Y.; Fukui, T.; Naka, K.; Chujo, Y. Tetrahedron Lett 2005, 46, 7011.
43. Onouchi, H.; Miyagawa, T.; Furuko, A.; Maeda, K.; Yashima, E. J Am Chem Soc 2005, 127, 2960.
44. Pietrusiewicz, K. M.; Zablocka, M. Chem Rev 1994, 94, 1375.
45. (a) Schrock, R. R.; Osborn, J. Inorg Chem 1970, 9, 2339;
46. (b) Kishimoto, Y.; Itou, M.; Miyatake, T.; Ikariya, T.; Noyori, R. Macromolecules 1995, 28, 6662.
47. As described in the experimental section, ca. two equivalents of propargylamine were added to a phosphonic dichloride, where a half amount of the amine was used as an HCl scavenger.
48. Percec, V.; Obata, M.; Rudick, J. G.; De, B. B.; Glodde, M.; Bera, T. K.; Magonov, S. N.; Balagurusamy, V. S. K.; Heiney, P. A. J Polym Sci, Part A: Polym Chem 2002, 40, 3509.
49. Sanda, F.; Araki, H.; Masuda, T. Macromolecules 2004, 37, 8510.
50. 3. After filtration of the polymer solutions using a membrane filter (pore size 0.45 μm), they exhibited the same CD spectra as the ones before filtration.