Synthesis and Polymerization of an Optically Active Bifunctional Disiloxane. 2. Preparation of Optically Active (S)-2-(1-Naphthyl)-2-phenyl-5,5-dimethyl-1-oxa-2,5-disilacyclopentane and Its Ring-Opening Polymerization

Macromolecules

Volumn 32, Issue 3, 1999, Pages 548-553

  Li, Yuning ^a   Kawakami, Yusuke ^a  

^a JAPAN ADVANCED INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC POLYMERS; INITIATORS (CHEMICAL); LITHIUM COMPOUNDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL PROPERTIES; RING OPENING POLYMERIZATION; SIZE EXCLUSION CHROMATOGRAPHY; SODIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

REGIOSELECTIVITY;

SILICONES;

EID: 0033537414     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma981300s     Document Type: Article

References (42)

1. (a) Miller, R. D.; Michl, J. Chem. Rev. 1989, 89, 1359.
2. (b) West, R. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley and Sons: New York, 1989; p 1207.
3. (c) Silicon-Containing Polymers; Richard, G. J., Ed.; The Royal Society of Chemistry: Cambridge, 1995.
4. (d) Birot, M.; Pillot, J.; Dunognes, J. Chem. Rev. 1995, 95, 1443.
5. (a) Weyenberg, D. R.; Nelson, L. E. J. Org. Chem. 1965, 30, 2618.
6. (b) Bamford, W. R.; Lovie, J. C.; Watt, J. A. C. J. Chem. Soc. C 1966, 1137.
7. (c) Nametkin, N. S.; Vdovin, V. M. Izv. Akad. Nauk SSSR, Ser. Khim. 1974, 1153.
8. (d) Matyjaszewski, K.; Chen, Y. L.; Kim, H. K. ACS Symp. Ser. 1988, 360, 78.
9. (e) Cypryk, M.; Gupta, Y.; Matyjazewski, K. J. Am. Chem. Soc. 1991, 113, 1046.
10. (f) Matyjazewski, K.; Cypryk, M.; Frey, H.; Hrkach, J.; Kim, H. K.; Moeller, M.; Ruehl, K.; White, M. J. Macromol. Sci., Chem. 1991, A28, 1151.
11. (a) Kriner, W. A. J. Polym. Sci., Polym. Chem. Ed. 1966, 4, 444.
12. (b) Nametkin, N. S.; Vdvin, V. M.; Zav'yalov, V. I. Dokl. Akad. Nauk SSSR, Ser. Khim. 1965, 162 (4), 824.
13. (c) Nametkin, N. S.; Vdvin, V. M.; Zelenaya, A. V. Dokl. Akad. Nauk SSSR, Ser. Khim. 1965, 162.
14. (d) Wu, H. J.; Interrante, L. V. Macromolecules 1992, 25, 1840.
15. (e) Suzuki, M.; Obayashi, T.; Kramer, W.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1994, 553.
16. (f) Suzuki, M.; Kotani, J.; Gyobu, S.; Kaneko, T.; Saegusa, T. Macromolecules 1994, 27, 2360.
17. (g) Suzuki, M.; Obayashi, T.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1993, 717.
18. (h) Suzuki, M.; Kaneko, T.; Morishima, Y.; Obayashi, T.; Saegusa, T. Polym. J. 1996, 28, 16.
19. (i) Interrante, L. V.; Liu, Q.; Rushkin, I.; Shen, Q. J. Organomet. Chem. 1996, 521, 1.
20. (j) Shen, Q. H.; Interrante, L. V.; J. Polym. Sci., Part A: Polym. Chem. 1997, 35, 3193.
21. (k) Uhlig, W. J. Polym. Sci., Part A: Polym. Chem. 1998, 36, 725.
22. (a) Armitage, D. A. In Comprehensive Organometallic Chemistry; Wlkinson, J., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, UK, 1982; Vol. 2, p 162.
23. (b) Barton, T. J. In Comprehensive Organometallic Chemistry; Wlkinson, J., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, UK, 1982; Vol. 2, p 205.
24. Corey, J. Y. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley and Sons: New York, 1989; pp 8-18.
25. (a) Hyde, J. F. U.S. Patent 2,490,357, 1949.
26. (b) Morton, M.; Deisz, M. A.; Bostick, E. E. J. Polym. Sci. 1962, A2, 513.
27. (c) Shinohara, M. Polym. Prepr. 1973, 1209.
28. (d) Chojnowski, J.; Mazurek, M. Makromol. Chem. 1975, 176, 2999.
29. (e) Molenberg, A.; Michalke, D.; Moller, M.; Pieper, T. J. Polym. Sci., Part A: Polym. Chem. 1998, 36, 169.
30. Piccoli, W. A.; Haberland, G. G.; Merker, R. L. J. Am. Chem. Soc. 1960, 82, 1883.
31. (a) Suryanarayana, B.; Peace, B. W.; Mayhan, K. G. J. Polym. Sci. 1974, 12, 1089.
32. (b) Suryanarayana, B.; Peace, B. W.; Mayhan, K. G. J. Polym. Sci. 1974, 12, 1109.
33. Samara, M.; Loy, D. A. Polym. Prep. 1998, 39 (1), 556.
34. Sommer, L. H.; Ansul, G. R. J. Am. Chem. Soc. 1955, 77, 2482.
35. Li, Y.; Kawakami, Y. Macromolecules 1998, 31, 5592.
36. Karstedt, B. D. U.S. Patent 3,775,452, 1973.
37. Ito, K.; Hashizuka, Y.; Yamashita, Y. Macromolecules 1977, 10, 821.
38. Compound 7 was prepared following the method reported by: Belmonte, P. A.; Own, Z. Y. J. Am. Chem. Soc. 1984, 106, 7493. Compound 9 was prepared by the procedure described in: Organic Syntheses; Noland, W. E., Ed.; John Wiley and Sons: New York, 1988; Vol. 6, p 354. Compounds 8 and 10 were prepared following the methods reported by: Sommer, L. H.; Frye, C. L.; Mosolf, M. C.; Parker, G. A.; Rodewald, P. G.; Michael, K. W.; Okaya, Y.; Pepinsky, R. J. Am. Chem. Soc. 1961, 83, 2210.
39. Compound 7 was prepared following the method reported by: Belmonte, P. A.; Own, Z. Y. J. Am. Chem. Soc. 1984, 106, 7493. Compound 9 was prepared by the procedure described in: Organic Syntheses; Noland, W. E., Ed.; John Wiley and Sons: New York, 1988; Vol. 6, p 354. Compounds 8 and 10 were prepared following the methods reported by: Sommer, L. H.; Frye, C. L.; Mosolf, M. C.; Parker, G. A.; Rodewald, P. G.; Michael, K. W.; Okaya, Y.; Pepinsky, R. J. Am. Chem. Soc. 1961, 83, 2210.
40. Compound 7 was prepared following the method reported by: Belmonte, P. A.; Own, Z. Y. J. Am. Chem. Soc. 1984, 106, 7493. Compound 9 was prepared by the procedure described in: Organic Syntheses; Noland, W. E., Ed.; John Wiley and Sons: New York, 1988; Vol. 6, p 354. Compounds 8 and 10 were prepared following the methods reported by: Sommer, L. H.; Frye, C. L.; Mosolf, M. C.; Parker, G. A.; Rodewald, P. G.; Michael, K. W.; Okaya, Y.; Pepinsky, R. J. Am. Chem. Soc. 1961, 83, 2210.
41. (a) Benouargha, A.; Boutevin, B.; Caporiccio, G.; Essassi, E.; Guida-Pietrasanta, F.; Ratsimihety, A. Eur. Polym. J. 1997, 33, 1117.
42. (b) Ameduri, B.; Boutevin, B.; Guida-Pietrasanta, F.; Manseri, A.; Ratsimihety, A.; Caporiccio, G. J. Polym. Sci., Part A: Polym. Chem. 1996, 34, 3077.