Synthesis of stereoregular and optically active polysiloxanes containing l, 3-dimethyl-l, 3-diphenyldisiloxane as a constitutional unit

Macromolecules

Volumn 33, Issue 6, 2000, Pages 1960-1963

  Oishi, Motoi ^a   Kawakami, Yusuke ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

MOLECULAR STRUCTURE; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYCONDENSATION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); THERMODYNAMIC STABILITY;

OPTICALLY ACTIVE POLYSILOXANE; STEREOREGULARITY;

SILICONES;

EID: 0033898158     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma991510k     Document Type: Article

References (28)

1. (a) Ito, Y.; Miyaké, T.; Ohara, T.; Suginome, M. Macromolécules 1998, 31, 1697.
2. (b) Nakano, T.; Satoh, Y.; Okamoto, Y. Polym. J. 1998, 30, 635.
3. Innis, P. C.; Noms, I. D.; Kane-Magurie, L. A. P.; Wallace, G. G. Macromolecules 1998, 31, 6521.
4. Tang, H.; Baba, M.; Imae, L; Kawakami, Y. Polym. J. 1999, 31, 313.
5. (e) Sogah, D. Y.; Zheng, S. Polym. Prepr. 1999, 40, 540.
6. (a) Kawakami, Y.; Takeyama, K.; Komuro, K.; Ooi, O. Macromoleclues 1998, 31, 551.
7. (b) Kawakami, Y.; Takahasi, T.; Yada, Y; Imae, I. Polym. J. 1998, 31, 1001.
8. Li, Y.; Kawakami, Y. Macromolecules 1998, 31, 5592.
9. Li, Y.; Kawakami, Y. Macromolecules 1999, 32, 548.
10. (a) Finkelmann, H.; Ringsdof, H.; Wendorf, J. H. Makromol. Chem. 1978, 179, 273.
11. (b) Finkelmann, H.; Happ, M.; Portugal, M.; Ringsdof, H. Makromol. Chem. 1978, 179, 2541.
12. Finkelmann, H.; Rehage, G. Makromol. Chem., Rapid Comunn. 1980, 1, 31.
13. (a) Soga, K.; Arai, T.; Ban, H. T.; Uozumi, T. Macromol. Chem., Rapid Commun. 1995, 16, 905.
14. (b) Arai, T.; Ban, H. T.; Uozumi, T.; Soga, K. Macromol. Chem. Phys. 1997, 792, 229.
15. Arai, T.; Ban, H. T.; Uozumi, T.; Soga, K. J. Polym. Sci., Part A: Polym. Chem. 1998, 36, 421.
16. (a) Abed-Ali, S. S.; Brisdon, B. J.; England, R. J. Chem. Soc., Chem. Commun. 1987, 1565.
17. (b) Duplock, S. K.; Matison, J. G.; Swincer, A. G.; Warren, R, F. 0. J. Inorg. Organomet. Polym. 1991, 1, 361.
18. Getz, S.; Schneider, H. A. Makromol. Chetn. 1993, 194, 233.
19. Zhou, G. B.; Khan, J. M.; Ishrant, M.; Smid, J. Macromolecules 1993, 26, 2202.
20. Oishi, M.; Kawakami, Y. Org. Lett. 1999, 1, 549.
21. (a) Pike, R. M. J. Polym. Sci. 1961, 50, 151.
22. (b) Stevvart, D. D.; Deters, E. N.; Bead, C. D.; Dunks, G. B.; Hedaya, E.; Kwiatkowski, G. T.; Moffitt, R. B.; Bohan, J. Macromolecules 1979, 12, 373.
23. Babu, G. N.; Newmark, R. A. Macromolecules 1991, 24, 4503.
24. (a) Sommer, L. H.; Frye, C. L.; Parker, G. A.; Michael, K W. J. Am. Chem. Soc. 1964, 86, 3271.
25. (b) Enantiomer excess was determined by HPLC analysis (Daicel Chem. Ind., CHIRALCEL ÖD, n-hexane:2-propanol =10:1 äs an eluent, 0.4 ml/min, 254 nm).
26. Sommer, L. H.; Citron, J. D.; Frye, C. L. J. Am. Chem. Soc. 1964, 86, 5685.
27. Experimental procedure and NMR and IR data for (S, S)diisotactic PI: A solution of 5a (0.1057 g, 0.74 mmol) in toluene (0.74 mL) was added to (S, S)-l (0.2158 g, 0.74 mmol). The reaction mixture was stirred at 100 °C for 24 h with N2 bubbling. After pouring into methanol, the precipitate was collected and dried in vacuo to give the polymer (0.1232 g, 48% yield). 1H NMR (500 MHz, CDC13): à-0.18 to 0.04 (br, 6H), 0.19 (minor) and 0.22 (major) (2s, 6H), 7.11-7.23 (br, 4H), 7.23-7.34 (br, 2H), 7.36-7.56 (br, 4H). 13C NMR (75 MHz, CDC13): <5 -0.27, 0.99, 127.7, 130.0, 133.5, 137.5. 29Si NMR (79 MHz, CDC13): <5 -34.3, -20.3. IR (neat, cm-1): 3093, 3072, 3026, 2963, 2765, 1593, 1429, 1125, 1097, 1021.
28. NMR and IR data for (fl, fl)-diisotactic P2: W NMR (500 MHz, CDC13): 0 -0.23-0.14 (br, 6H), 6.74-7.11 (br, 8H), 7.11-7.46 (br, 12H). 13C NMR (75 MHz, CDC13): <5 -0.51, 127.6, 127.7, 129.6, 129.9, 133.5 (overlap), 134.5, 134.6. 29Si NMR (79 MHz, CDC13): <5 -46.8, -33.5. IR (neat, cm-1): 3071, 3051, 3026, 3004, 2962, 2904, 1592, 1429, 1126, 1024.