Kinetic control of "unnatural" chiral induction in poly(isocyanide)s

Advanced Materials

Volumn 10, Issue 13, 1998, Pages 1001-1005

  Amabilino, David B ^a   Ramos, Elena ^a   Serrano, José Luis ^b   Veciana, Jaume ^a  

^a INSTITUT DE CIÈNCIA DE MATERIALS DE BARCELONA ICMAB CSIC   (Spain)

^b UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

MOLECULAR STRUCTURE; MONOMERS; NITROGEN COMPOUNDS; REACTION KINETICS;

CHIRAL INDUCTION; POLYISOCYANIDE;

ORGANIC POLYMERS;

EID: 0032164163     PISSN: 09359648     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-4095(199809)10:13<1001::AID-ADMA1001>3.0.CO;2-Y     Document Type: Article

References (50)

1. a) Polymeric Materials Encyclopedia: Synthesis, Properties and Applications (Ed. J. C. Salamone), CRC Press, Boca Raton, FL 1996.
2. Recent reviews: b) H. H. Brintzinger, D. Fischer, R. Mülhaupt, B. Rieger, R. M. Waymouth, Angew. Chem. 1995, 107, 1255; Angew. Chem. Int. Ed. Engl. 1995, 34, 1143.
3. Recent reviews: b) H. H. Brintzinger, D. Fischer, R. Mülhaupt, B. Rieger, R. M. Waymouth, Angew. Chem. 1995, 107, 1255; Angew. Chem. Int. Ed. Engl. 1995, 34, 1143.
4. c) M. Leclerc, K. Faïd, Adv. Mater. 1997, 9, 1087.
5. d) S. J. Higgins, Chem. Soc. Rev. 1997, 26, 247.
6. e) J. D. Stenger-Smith, Prog. Polym. Sci. 1998, 23, 57.
7. Other recent pertinent examples: f) L. X. Wang, T. Soczka-Guth, E. Havinga, K. Müllen, Angew. Chem. 1996, 108, 1602; Angew. Chem. Int. Ed. Engl. 1996, 35, 1495.
8. Other recent pertinent examples: f) L. X. Wang, T. Soczka-Guth, E. Havinga, K. Müllen, Angew. Chem. 1996, 108, 1602; Angew. Chem. Int. Ed. Engl. 1996, 35, 1495.
9. g) E. Peeters, A. Delmotte, R. A. J. Janssen, E. W. Meijer, Adv. Mater. 1997, 9, 493.
10. a) A. Klug, Angew. Chem. Int. Ed. Engl. 1983, 22, 565.
11. b) D. W. Urry, Angew. Chem. Int. Ed. Engl. 1993, 32, 819.
12. c) J. G. Tirrell, M. J. Fournier, T. L. Mason, D. A. Tirrell, Chem. Eng. News 1994, December 19, 40.
13. a) M. N. Teerenstra, R. D. Klap, M. J. Bijl, A. J. Schouten, R. J. M. Nolte, T. Verbiest, A. Persoons, Macromolecules 1996, 29, 4871.
14. b) M. N. Teerenstra, J. G. Hagting, A. J. Schouten, R. J. M. Nolte, M. Kauranen, T. Verbiest, A. Persoons, Macromolecules 1996, 29, 4876.
15. c) C. N. Bowman, C. A. Guymon, MRS Bull. 1997, 22(9), 15.
16. d) T. J. Deming, Adv. Mater. 1997, 9, 299.
17. e) Q.-S. Hu, W.-S. Huang, D. Vitharana, X.-F. Zheng, L. Pu, J. Am. Chem. Soc. 1997, 119, 12 454.
18. f) T. Jaworek, D. Neher, G. Wegner, R. H. Wieringa, A. J. Schouten, Science 1998, 279, 57.
19. Reviews: a) F. Millich J. Polym. Sci., Part D: Macromol. Rev. 1980, 15, 207.
20. b) R. J. M. Nolte, Chem. Soc. Rev. 1994, 23, 11.
21. See also: c) R. B. King, L. Borodinsky, Macromolecules 1985, 18, 2117.
22. d) M. Abdelkader, W. Drenth, E. W. Meijer, Chem. Mater. 1991, 3, 598.
23. e) B. Hong, M. A. Fox, Macromolecules 1994, 27, 5311.
24. f) J.-T. Huang, J. Sun, W. B. Euler, W. Rosen, J. Polym. Sci., Part A: Polym. Chem. 1997, 35, 439.
25. R. J. M. Nolte, A. J. M. van Beijnen, W. Drenth. J. Am. Chem. Soc. 1974, 96, 5932.
26. a) A. J. M. van Beijnen, R. J. M. Nolte, W. Drenth, A. M. F. Hezemans, Tetrahedron 1976, 32, 2017.
27. b) A. J. M. van Beijnen, R. J. M. Nolte, A. J. Naaktegeboren, J. W. Zwikker, W. Drenth, A. M. F. Hezemans, Macromolecules 1983, 16, 1679.
28. c) M. M. Green, R. A. Gross, F. C. Schilling, K. Zero, C. Crosby III, Macromolecules 1988, 21, 1839.
29. d) D. Pini, A. Iuliano, P. Salvadori, Macromolecules 1992, 25, 6059.
30. P. C. J. Kamer, R. J. M. Nolte, W. Drenth, J. Am. Chem. Soc. 1988, 110, 6818.
31. P. C. J. Kamer, M. C. Cleij, R. J. M. Nolte, T. Harada, A. M. F. Hezemans, W. Drenth, J. Am. Chem. Soc. 1988, 110, 1581.
32. E. Ramos, J. Bosch, J.-L. Serrano, T. Sierra, J. Veciana, J. Am. Chem. Soc. 1996, 118, 4703.
33. For another recent example, see: J. P. Chen, J. P. Gao, Z. Y. Wang, Polym. Int. 1997, 44, 83.
34. D. B. Amabilino, E. Ramos, J.-L. Serrano, T. Sierra, J. Veciana, J. Am. Chem. Soc., in press.
35. a) M. M. Green, N. C. Peterson, T. Sato, A. Teramoto, R. Cook, S. Lifson, Science 1995, 268, 1860.
36. b) N. Okamoto, F. Mukaida, H. Gu, Y. Nakamura, T. Sato, A. Teramoto, M. M. Green, C. Andreola, N. C. Peterson, S. Lifson, Macromolecules 1996, 29, 2878.
37. c) J. V. Selinger, R. L. B. Selinger, Phys. Rev. Lett. 1996, 76, 58.
38. d) M. Müller, R. Zentel, Macromolecules 1996, 29, 1609.
39. e) K. Obata, C. Kabuto, M. Kira, J. Am. Chem. Soc. 1997, 119, 11 345.
40. a) H. Stegemeyer, K. J. Mainush, Naturwissenschaften 1971, 58, 599.
41. b) F. D. Saeva, P. E. Sharpe, G. R. Olin, J. Am. Chem. Soc. 1973, 95, 7656.
42. c) G. Gottarelli, B. Samori, S. Marzocchi. Tetrahedron Lett. 1975, 1981.
43. d) K. Yamada, Y. Takanishi, K. Ishikawa, H. Takezoe, A. Fukuda, M. A. Osipov, Phys. Rev. E 1997, 56, R43.
44. e) A. R. A. Palmans, J. A. J. M. Vekemans, E. E. Havinga, E. W. Meijer, Angew. Chem. 1997, 109, 2763; Angew. Chem. Int. Ed. Engl. 1997, 36, 2648.
45. e) A. R. A. Palmans, J. A. J. M. Vekemans, E. E. Havinga, E. W. Meijer, Angew. Chem. 1997, 109, 2763; Angew. Chem. Int. Ed. Engl. 1997, 36, 2648.
46. Use of "living" catalysts for the polymerization of chiral isocyanides, in which the chiral center was relatively close to the isocyanide group, was shown to pass on the helical sense of the backbone in the polymer to achiral monomeric units, see: F. Takei, K. Yanai, K. Onitsuka, S. Takahashi, Angew. Chem. Int. Ed. Engl. 1996, 35, 1554.
47. It is not clear whether the observed variance of optical activity with ee of the monomers is a result of the formation of pure M helices from monomeric units with only R configuration, and pure P helices with S monomers (i.e., isotactic polymer), or whether the macromolecules contain unequal mixtures of R and S monomeric units and helix reversals.
48. T. J. Deming, B. M. Novak, Macromolecules 1993, 26, 7092.
49. R. Urbau, D. Marquarding, P. Seidel, I. Ugi, A. Weindelt, Chem. Ber. 1977, 110, 2012.
50. M are the proportions of the M and P helices, respectively. From this expression, and bearing the assumptions stated in mind, we calculate an approximate value for the diastereomeric excess of the P helix in (S)-2B of 91%. Using the same reasoning, the diastereomeric excess of the P helix for (5)-2A is approximately 24%.