Novel palladium-catalyzed polycondensation of propargyl carbonates and bisphenols. Synthesis of polyethers having exomethylene groups

Macromolecules

Volumn 37, Issue 26, 2004, Pages 9670-9672

  Koizumi, Toshio ^a   Sugie, Koji ^a   Kiyonaga, Osami ^a   Yamanaka, Masaomi ^a   Kawabata, Satoshi ^a  

^a NATIONAL DEFENSE ACADEMY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYSIS; CATALYSTS; INFRARED SPECTROSCOPY; METHANOL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PALLADIUM; PHENOLS; POLYCARBONATES; POLYCONDENSATION; POLYETHERS; POLYMERIZATION; SYNTHESIS (CHEMICAL);

BISPHENOLS; EXOMETHYLENE GROUPS; POLYADDITION REACTIONS; PROPARGYL CARBONATES;

ORGANIC POLYMERS;

EID: 11444267044     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma040110g     Document Type: Article

References (24)

1. (a) Tsuji, J. In Palladium Reagents and Catalysts, Innovations in Organic Synthesis; John Wiley: New York, 1995; p 290.
2. (b) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
3. (a) Suzuki, M.; Lim, J.-C.; Oguni, M.; Eberhardt, A.; Saegusa, T. Polym. J. 1990, 22, 818.
4. (b) Suzuki, M.; Ii, A.; Saegusa, T. Macromolecules 1992, 25, 7071.
5. Suzuki, M.; Sawada, S.; Yoshida, S.; Eberhardt, A.; Saegusa, T. Macromolecules 1993, 26, 4748.
6. (a) Miyaki, N.; Tomita, I.; Kido, J.; Endo, T. Macromolecules 1997, 30, 4504.
7. (b) Miyaki, N.; Tomita, I.; Endo, T. J. Polym. Sci., Part A: Polym. Chem. 1997, 35, 2097.
8. (a) Nomura, N.; Tsurugi, K.; Okada, M. J. Am. Chem. Soc. 1999, 121, 7268.
9. (b) Nomura, N.; Yoshida, N.; Tsurugi, K.; Aoi, K. Macromolecules 2003, 36, 3007.
10. (a) Koizumi, T.; Sakamoto, J.; Gondo, Y.; Endo, T. Macromolecules 2002, 35, 2898.
11. (b) Koizumi, T.; Sakamoto, J.; Gondo, Y.; Endo, T. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 2487.
12. Koizumi, T.; Imai, T.; Endo, T. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 476.
13. Koizumi, T.; Koma, Y.; Endo, T. Macromolecules 2003, 36, 5882.
14. (a) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589.
15. (b) Tsuji, J.; Watanabe, H.; Minami, I.; Shimizu, I. J. Am. Chem. Soc. 1985, 107, 2196.
16. Minami, I.; Yuhara, M.; Watanabe, H.; Tsuji, J. J. Organomet. Chem. 1987, 334, 225.
17. Labrosse, J.-R.; Lhoste, P.; Sinou, D. J. Org. Chem. 2001, 66, 6634.
18. 3-propargylpalladium intermediates, see: (a) Su, C.-C.; Chen, J.-T.; Lee, G. H.; Wang. Y. J. Am. Chem. Soc. 1994, 116, 4999. (b) Casey, C. P.; Nash, J. R.; Yi, C. S.; Selmeczy, A. D.; Chung, S.; Powell, D. R.; Hayashi, R. K. J. Am. Chem. Soc. 1998, 120, 722. (c) Tsutsumi, K.; Ogoshi, S.; Nishiguchi, S.; Kurosawa, H. J. Am. Chem. Soc. 1998, 120, 1938.
19. 3-propargylpalladium intermediates, see: (a) Su, C.-C.; Chen, J.-T.; Lee, G. H.; Wang. Y. J. Am. Chem. Soc. 1994, 116, 4999. (b) Casey, C. P.; Nash, J. R.; Yi, C. S.; Selmeczy, A. D.; Chung, S.; Powell, D. R.; Hayashi, R. K. J. Am. Chem. Soc. 1998, 120, 722. (c) Tsutsumi, K.; Ogoshi, S.; Nishiguchi, S.; Kurosawa, H. J. Am. Chem. Soc. 1998, 120, 1938.
20. 3-propargylpalladium intermediates, see: (a) Su, C.-C.; Chen, J.-T.; Lee, G. H.; Wang. Y. J. Am. Chem. Soc. 1994, 116, 4999. (b) Casey, C. P.; Nash, J. R.; Yi, C. S.; Selmeczy, A. D.; Chung, S.; Powell, D. R.; Hayashi, R. K. J. Am. Chem. Soc. 1998, 120, 722. (c) Tsutsumi, K.; Ogoshi, S.; Nishiguchi, S.; Kurosawa, H. J. Am. Chem. Soc. 1998, 120, 1938.
21. -1.
22. Nomura reported the Pd-catalyzed polycondensation of allylic compounds and nucleophiles under stoichiometrically imbalanced conditions: (a) Nomura, N.; Tsurugi, K.; Okada, M. Angew. Chem., Int. Ed. 2001, 40, 1932. (b) Tsurugi, K.; Nomura, N.; Aoi, K. Tetrahedron Lett. 2002, 43, 469.
23. Nomura reported the Pd-catalyzed polycondensation of allylic compounds and nucleophiles under stoichiometrically imbalanced conditions: (a) Nomura, N.; Tsurugi, K.; Okada, M. Angew. Chem., Int. Ed. 2001, 40, 1932. (b) Tsurugi, K.; Nomura, N.; Aoi, K. Tetrahedron Lett. 2002, 43, 469.
24. 1H NMR spectra of 4bf and 4bg.