Three-component coupling polymerization of bisallene, aryl dihalide, and nucleophiles via π-allylpalladium complex

Macromolecules

Volumn 29, Issue 21, 1996, Pages 6685-6690

  Miyaki, Nobuyuki ^a   Tomita, Ikuyoshi ^a   Endo, Takeshi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CATALYSTS; HALOGEN COMPOUNDS; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; ORGANIC SOLVENTS; PALLADIUM;

ARYL DIHALIDE; BISALLENE; COUPLING POLYMERIZATION; NUCLEOPHILES;

TERPOLYMERIZATION;

EID: 0030573863     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma9504431     Document Type: Article

References (27)

1. (a) Leland, J.; Boucher, J.; Anderson, K. J. Polym. Sic., Polym. Ed. 1977,15, 2785.
2. (b) Yokozawa, T.; Ito, N.; Endo, T. Chem. Lett. 1988, 233.
3. (c) Aggour, Y. A.; Tomita, I.; Endo, T. Makromol. Chem. 1993, 194, 3323.
4. Takahashi, T.; Yokozawa, T.; Endo, T. Makromol. Chem. 1991, 192, 1207.
5. Tomita, I.; Kondo, Y.; Takagi, K.; Endo, T. Macromolecules 1994, 27, 4413.
6. (a) Tsuji, J. Organic Synthesis with Palladium Compounds; Springer-Verlag: Berlin, 1980.
7. (b) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985.
8. (a) Ahmar, M.; Cazes, B.; Gore, J. Tetrahedron Lett. 1984, 25, 4505.
9. (b) Shimizu, I.; Tsuji, J. Chem. Lett. 1984, 233.
10. (c) Trost, B. M. Acc. Chem. Res. 1980, 13, 385.
11. (d) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173.
12. (e) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33 2379.
13. (a) Yoneyama, M.; Kakimoto, M.; Imai, Y Macromolecules 1988, 21, 1908.
14. (b) Idem., ibid. 1989, 22, 2593.
15. Patai, S. The Chemistry of Ketenes, Allenes, and Related Compounds; Elsevier Scientific Publishing Company: New York, 1981. Brandsma, L.; Verkruijsse, H. D. Synthesis of Acetylenes, Allenes and Cumulenes; Preface Ltd., New York, 1981.
16. Patai, S. The Chemistry of Ketenes, Allenes, and Related Compounds; Elsevier Scientific Publishing Company: New York, 1981. Brandsma, L.; Verkruijsse, H. D. Synthesis of Acetylenes, Allenes and Cumulenes; Preface Ltd., New York, 1981.
17. Although, the formation of an exo-isomer was not mentioned in ref 5a, the peaks at 5.30 and 5.06 ppm are illustrative of the existence of the exo-isomer.
18. 1H-NMR spectrum (Figure 1) can be attributed to the protons of methylenes adjacent to the Z-isomeric double bond.
19. Trost, B. M. Tetrahedron 1977, 33, 2615.
20. n = 2,900) than that obtained by the Pd(II) catalyst.
21. Perry, J. R; Wilson, D. B. Macromolecules 1993, 26, 1503.
22. In this case, the homocoupling product, terphenyl, should be also produced; however, it did not appear with GC because of its high boiling point.
23. Uno, M.; Sato, K.; Masuda, M.; Ueda, W.; Takahashi S. Tetrahedron Lett. 1985, 26, 1553.
24. Wallow, T. I.; Novak, B. M. ACS Polym, Prep. 1993, 34, 1008.
25. (a) Fauvarque, J.-F.; Pflüger, F.; Troupel, M. J. Organomet. Chem. 1981, 208, 419.
26. (b) Amatore, C.; Pflüger, F. Organometallics 1990, 9, 2276.
27. The para-substituents probably affected the rate-determining step (the insertion of allene moieties or the nucleophilic attack), because the preceding oxidative addition is known to be a very fast step and to become faster as the electronwithdrawing character of substituent is increased. See, ref 16.