Screw-sense-selective polymerization of aryl isocyanides initiated by a Pd-Pt μ-ethynediyl dinuclear complex: A novel method for the synthesis of single-handed helical poly(isocyanide)s with the block copolymerization technique

Chemistry - A European Journal

Volumn 6, Issue 6, 2000, Pages 983-993

  Takei, Fumie ^a   Yanai, Koichi ^a   Onitsuka, Kiyotaka ^a   Takahashi, Shigetoshi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Acetylide complexes; Chirality; Helical structures; Isocyanides; Polymerizations

Indexed keywords

CYANIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; KINETICS; POLYMERIZATION; THERMODYNAMICS;

EID: 0034677682     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(20000317)6:6<983::AID-CHEM983>3.0.CO;2-P     Document Type: Article

References (87)

1. C. R. Cantor, R. Schimmel, Biophysical Chemistry, Part I: The Conformation of Biological Macromolecules, W. H. Freeman and Co., New York, 1980.
2. a) O. Vogl, G. D. Jaycox, CHEMTECH 1986, 16, 698;
3. b) G. Wulff, Angew. Chem. 1989, 101, 22;
4. Angew. Chem. Int. Ed. Engl. 1989, 25, 21;
5. c) Y. Okamoto, T. Nakano, Chem. Rev. 1994, 94, 349.
6. a) H. Yuki, K. Ohta, Y. Okamoto, K. Hatada, J. Polym. Sci. Polym. Lett. Ed. 1977, 15, 589;
7. b) K. Ohta, K. Hatada, Y. Okamoto, H. Yuki, J. Polym. Sci. Polym. Lett. Ed. 1978, 16, 545;
8. c) Y. Okamoto, K. Suzuki, K. Ohta, K. Hatada, H. Yuki, J. Am. Chem. Soc. 1979, 101, 4763;
9. d) Y. Okamoto, K. Suzuki, H. Yuki, J. Polym. Sci. Polym. Chem. Ed. 1980, 18, 3043;
10. e) Y. Okamoto, H. Shohi, H. Yuki, J. Polym. Sci. Polym. Lett. Ed. 1983, 21, 601;
11. f) Y. Okamoto, E. Yashima, T. Nakano, K. Hatada, Chem. Lett. 1987, 759;
12. g) Y. Okamoto, E. Yashima, M. Ishikura, K. Hatada, Polym. J. 1987, 19, 1183;
13. h) S. Kanoh, N. Kawaguchi, T. Sumino, Y. Hongo, H. Suda, J. Polym. Sci. Part A, Polym. Chem. 1987, 25, 1603;
14. i) S. Kanoh, T. Sumino, N. Kawaguchi, M. Motoi, H. Suda, Polym. J. 1988, 20, 539;
15. j) T. Nakano, Y. Okamoto, K. Hatada, J. Am. Chem. Soc. 1992, 114, 1318
16. k) Y. Okamoto, M. Nishikawa,T. Nakano, E. Yashima, K. Hatada, Macromolecules 1995, 28, 5135;
17. l) S. Habue, T. Tanaka, Y. Okamoto, Macromolecules 1995, 28, 5973;
18. m) T. Nakano, Y. Okamoto, K. Hatada, Polymer J. 1995, 27, 892;
19. n) T. Nakano, Y. Shikisai, Y. Okamoto, Polymer J. 1996, 25, 51.
20. a) M. Goodman, S.-C. Chen, Macromolecules 1970, 3, 398;
21. b) M. Goodman, S.-C. Chen, Macromolecules 1971, 4, 625;
22. c) A. Bur, L. Fetters, Chem. Rev. 1976, 76, 727;
23. d) M. M. Green, M. P. Reidy, R. J. Johnson, G. Darling, D. J. O'Leary, G. Wilson, J. Am. Chem. Soc. 1989, 111, 6452;
24. e) S. Lifson, C. E. Felder, M. M. Green, Macromolecules 1992, 25, 4142;
25. f) Y. Okamoto, M. Matsuda, T. Nakano, E. Yashima, J. Polym. Sci. Part A: Polym. Chem. 1994, 32, 309;
26. g) M. M. Green, N. C. Peterson, T. Sato, A. Teramoto, R. Cook, S. Lifson, Science 1995, 268, 1860;
27. h) M. Müller, R. Zentel, Macromolecules 1996, 29, 1609.
28. a) O. Vogl, H. C. Miller, W. H. Sharkey, Macromolecules 1972, 5, 658;
29. b) O. Vogl, F. Xi, K. Ute, T. Nishimura, K. Hatada, Macromolecules 1989, 22, 4660;
30. c) K. Ute, K. Hirose, H. Kashimoto, K. Hatada, O. Vogl, J. Am. Chem. Soc. 1991, 113, 6305.
31. a) H. Yuki, Y. Okamoto, I. Okamoto, J. Am. Chem. Soc. 1980, 102, 6358;
32. b) Y. Okamoto, I. Okamoto, H. Yuki, Chem. Lett. 1981, 835;
33. c) Y. Okamoto, S. Honda, I. Okamoto, H. Yuki, S. Murata, R. Noyori, H. Takaya, J. Am. Chem. Soc. 1981, 103, 6971;
34. d) Y. Okamoto, E. Yashima, K. Hatada, K. Mislow, J. Org. Chem. 1984, 49, 557;
35. e) Y. Okamoto, CHEMTECH 1987, 17, 698;
36. f) C. Ren, C. Chen, F. Xi, T. Nakano, Y. Okamoto, J. Polym. Sci., Part A: Polym. Chem. 1993, 31, 2721.
37. G. Maxein, H. Keller, B. M. Novak, R. Zentel, Adv: Mater. 1998, 10, 341.
38. a) F. Millich, Chem. Rev. 1972, 72, 101;
39. b) F. Millich, Adv. Polym. Sci. 1975, 19, 117;
40. W. Drenth, R. J. M. Nolte, Acc. Chem. Res. 1979, 12, 30;
41. d) R. J. M. Nolte, Chem. Soc. Rev. 1994, 11.
42. R. J. M. Nolte, A. J. M. van Beijnen, J. W. Zwikker, J. Am. Chem. Soc. 1974, 96, 5932.
43. a) F. Millich, G. K. Baker, Macromolecules 1969, 2, 122;
44. b) A. J. M. van Beijnen, R. J. M. Nolte, W. Drenth, A. M. F. Hezemans, Tetrahedron 1976, 32, 2017;
45. c) R. J. M. Nolle, J. A. J. van Zomeren, W. Drenth, J. Org. Chem. 1978, 43, 1972;
46. d) A. J. M. van Beijnen, R. J. M. Nolte, J. W. Zwikker, W. Drenth, J. Mol. Catal. 1978, 4, 427;
47. e) A. J. M. van Beijnen, R. J. M. Nolte, W. Drenth, A. M. F. Hezemans, P. J. F. M. van de Coolwijk, Macromolecules 1980, 13, 1386;
48. f) A. J. M. van Beijnen, R. J. M. Nolte, A. J. Naaktgeboren, J. M. Ziwikker, W. Drenth, A. M. F. Hezemans, Macromolecules 1983, 16, 1679;
49. g) D. Pini, A. Iuliano, P. Salvadori, Macromolecules 1992, 25, 6059.
50. a) P. C. J. Kamer, R. J. M. Nolte, W. Drenth, J. Chem. Soc. Chem. Commun. 1986, 1789;
51. b) P. C. J. Kamer, R. J. M. Nolte, W. Drenth, J. Am. Chem. Soc. 1988, 110, 6818.
52. a) T. Harada, M. C. Cleij, R. J. M. Nolte, A. M. F. Hezemans, W. Drenth, J. Chem. Soc. Chem. Commun. 1984, 726;
53. b) 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.
54. a) T. J. Deming, B. M. Novak, J. Am. Chem. Soc. 1992, 114, 4400;
55. b) T. J. Deming, B. M. Novak, J. Am. Chem. Soc. 1992, 114, 7926.
56. a) Y. Ito, E. Ihara, M. Murakami, M. Shiro, J. Am. Chem. Soc. 1990, 112, 6446;
57. b) Y. Ito, E. Ihara, M. Murakami, Angew: Chem. 1992, 104, 1508;
58. Angew. Chem. Int. Ed. Engl. 1992, 31, 1509;
59. c) Y. Ito, E. Ihara, M. Murakami, M. Sisido, Macromolecules 1992, 25, 6810;
60. d) Y. Ito, Y. Kojima, M. Murakami, Tetrahedron Lett. 1993, 34, 8279.
61. e) Y. Ito, Y. Kojima, M. Suginome, M. Murakami, Heterocycles, 1996, 42, 597;
62. f) Y. Ito, Y. Kojima, M. Murakami, M. Suginome, Bull. Chem. Soc. Jpn. 1997, 70, 2801.
63. a) Y. Ito, T. Ohara, R. Shima, M. Suginome, J. Am. Chem. Soc. 1996, 118, 9188;
64. b) Y. Ito, T. Miyake, T. Ohara, M. Suginome, Macromolecules 1998, 31, 1697;
65. c) Y. Ito, T. Miyake, S. Hatano, R. Shima, T. Ohara, M. Suginome, J. Am. Chem. Soc. 1998, 120, 11880.
66. a) K. Onitsuka, T. Joh, S. Takahashi, Angew. Chem. 1992, 104, 893;
67. Angew. Chem. Int. Ed. Engl. 1992, 31, 851;
68. b) K. Onitsuka, K. Yanai, F. Takei, T. Joh, S. Takahashi, Organometallics, 1994, 13, 3862.
69. F. Takei, K. Yanai, K. Onitsuka, S. Takahashi, Angew. Chem. 1996, 108, 1643;
70. Angew. Chem. Int. Ed. Engl. 1996, 35, 1554.
71. 2. See the Experimental Section.
72. M. Tokunaga, M. Eckert, Y. Wakatsuki, Angew. Chem. 1999, 111, 3416;
73. Angew. Chem. Int. Ed. 1999, 38, 3222.
74. a) J. H. Brewster, J. Am. Chem. Soc. 1959, 81, 5475;
75. b) J. H. Brewster, Topics in Stereochemistry, 1967, 2, 1.
76. a) E. Ramos, J. Bosch, J.-L. Serrano, T. Sierra, J. Veciana, J. Am. Chem. Soc. 1996, 118, 4703;
77. b) D. B. Amabilino, E. Ramos, J.-L. Serrano, T. Sierra, J. Veciana, J. Am. Chem. Soc. 1998, 120, 9126.
78. a) K. Maeda, Y. Okamoto, Macromolecules, 1998, 31, 1046;
79. b) K. Maeda, Y. Okamoto, Macromolecules, 1999, 32, 974.
80. a) H. Gu, Y. Nakamura, T. Sato, A. Teramoto, M. M. Green, C. Andreola, N. C. Peterson, S. Lifson, Macromolecules 1995, 28, 1016;
81. 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.
82. M. M. Green, R. A. Gross, F. C. Schilling, K. Zero, C. Crosby III, Macromolecules 1988, 21, 1839.
83. a) C. Kollmar, R. Hoffman, J. Am. Chem. Soc. 1990, 112, 8230;
84. b) M. Clericuzio, G. Alagona, C. Ohio, P. Salvadori, J. Am. Chem. Soc. 1997, 119, 1059.
85. J. C. Sheehan, D.-D. H. Yang, J. Am. Chem. Soc. 1958, 80, 1154.
86. R. Obrecht, R. Herrmann, I. Ugi, Synthesis, 1985, 400.
87. K. Onitsuka, T. Joh, S. Takahashi, Bull. Chem. Soc. Jpn. 1992, 65, 1179.