Cyclocopolymerization of α,ω-Dienes with Carbon Monoxide Catalyzed by (R,S)-BINAPHOS-Pd(II)

Bulletin of the Chemical Society of Japan

Volumn 70, Issue 3, 1997, Pages 659-664

  Nozaki, Kyoko ^a   Sato, Naomasa ^a   Nakamoto, Koji ^a   Takaya, Hidemasa ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000400997     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.70.659     Document Type: Article

References (30)

1. General references for the copolymerization of olefins with carbon monoxide: a) E. Drent and P. H. M. Budzelaar, Chem. Rev., 96, 663 (1996); b) A. Sen, Acc. Chem. Res., 26, 303 (1993); c) E. Drent, J. A. M. van Broekhovenm, and M. J. Doyle, J. Organomet. Chem., 417, 235 (1991), and references cited therein. Mechanistic aspects of the alternating nature of the present reaction was studied by Brookhart. d) F. C. Rix, M. Brookhart, and P. S. White, J. Am. Chem. Soc., 118, 4746 (1996).
2. General references for the copolymerization of olefins with carbon monoxide: a) E. Drent and P. H. M. Budzelaar, Chem. Rev., 96, 663 (1996); b) A. Sen, Acc. Chem. Res., 26, 303 (1993); c) E. Drent, J. A. M. van Broekhovenm, and M. J. Doyle, J. Organomet. Chem., 417, 235 (1991), and references cited therein. Mechanistic aspects of the alternating nature of the present reaction was studied by Brookhart. d) F. C. Rix, M. Brookhart, and P. S. White, J. Am. Chem. Soc., 118, 4746 (1996).
3. General references for the copolymerization of olefins with carbon monoxide: a) E. Drent and P. H. M. Budzelaar, Chem. Rev., 96, 663 (1996); b) A. Sen, Acc. Chem. Res., 26, 303 (1993); c) E. Drent, J. A. M. van Broekhovenm, and M. J. Doyle, J. Organomet. Chem., 417, 235 (1991), and references cited therein. Mechanistic aspects of the alternating nature of the present reaction was studied by Brookhart. d) F. C. Rix, M. Brookhart, and P. S. White, J. Am. Chem. Soc., 118, 4746 (1996).
4. General references for the copolymerization of olefins with carbon monoxide: a) E. Drent and P. H. M. Budzelaar, Chem. Rev., 96, 663 (1996); b) A. Sen, Acc. Chem. Res., 26, 303 (1993); c) E. Drent, J. A. M. van Broekhovenm, and M. J. Doyle, J. Organomet. Chem., 417, 235 (1991), and references cited therein. Mechanistic aspects of the alternating nature of the present reaction was studied by Brookhart. d) F. C. Rix, M. Brookhart, and P. S. White, J. Am. Chem. Soc., 118, 4746 (1996).
5. Some examples for the functionalization of poly(olefins-alt-CO), reviews: a) A. Sen, Adv. Polym. Sci., 73/74, 125 (1986); b) A. Sen, CHEMTECH, 1986, 48. Other references: c) M. M. Brubaker, D. D. Coffman, and H. H. Hoehn, J. Am. Chem. Soc., 74, 1509 (1952); d) M. J. Green, A. R. Lucy, S. Lu, and R. M. Paton, J. Chem. Soc., Chem. Commun., 1994, 2063.
6. Some examples for the functionalization of poly(olefins-alt-CO), reviews: a) A. Sen, Adv. Polym. Sci., 73/74, 125 (1986); b) A. Sen, CHEMTECH, 1986, 48. Other references: c) M. M. Brubaker, D. D. Coffman, and H. H. Hoehn, J. Am. Chem. Soc., 74, 1509 (1952); d) M. J. Green, A. R. Lucy, S. Lu, and R. M. Paton, J. Chem. Soc., Chem. Commun., 1994, 2063.
7. Some examples for the functionalization of poly(olefins-alt-CO), reviews: a) A. Sen, Adv. Polym. Sci., 73/74, 125 (1986); b) A. Sen, CHEMTECH, 1986, 48. Other references: c) M. M. Brubaker, D. D. Coffman, and H. H. Hoehn, J. Am. Chem. Soc., 74, 1509 (1952); d) M. J. Green, A. R. Lucy, S. Lu, and R. M. Paton, J. Chem. Soc., Chem. Commun., 1994, 2063.
8. Some examples for the functionalization of poly(olefins-alt-CO), reviews: a) A. Sen, Adv. Polym. Sci., 73/74, 125 (1986); b) A. Sen, CHEMTECH, 1986, 48. Other references: c) M. M. Brubaker, D. D. Coffman, and H. H. Hoehn, J. Am. Chem. Soc., 74, 1509 (1952); d) M. J. Green, A. R. Lucy, S. Lu, and R. M. Paton, J. Chem. Soc., Chem. Commun., 1994, 2063.
9. a) E. Amevor, S. Bronco, G. Consiglio, and S. Di Benedetto, Macromol. Symp., 89, 443 (1995);
10. b) S. Bronco, G. Consiglio, R. Hutter, A. Batistini, and U. W. Suter, Macromolecules, 27, 4436 (1994).
11. M. Brookhart, F. C. Rix, J. M. DeSimone, and J. C. Barborak, J. Am. Chem. Soc., 114, 5894 (1992).
12. Syntheses of chiral polymers from achiral monomers are of much interest as an effective process to obtain optically active materials: a) Y. Okamoto and T. Nakano, Chem. Rev., 94, 349 (1994); b) G. Wulff, Angew. Chem., Int. Ed. Engl., 28, 21 (1989); c) G. W. Coates and R. M. Waymouth, J. Am. Chem. Soc., 115, 91 (1993).
13. Syntheses of chiral polymers from achiral monomers are of much interest as an effective process to obtain optically active materials: a) Y. Okamoto and T. Nakano, Chem. Rev., 94, 349 (1994); b) G. Wulff, Angew. Chem., Int. Ed. Engl., 28, 21 (1989); c) G. W. Coates and R. M. Waymouth, J. Am. Chem. Soc., 115, 91 (1993).
14. Syntheses of chiral polymers from achiral monomers are of much interest as an effective process to obtain optically active materials: a) Y. Okamoto and T. Nakano, Chem. Rev., 94, 349 (1994); b) G. Wulff, Angew. Chem., Int. Ed. Engl., 28, 21 (1989); c) G. W. Coates and R. M. Waymouth, J. Am. Chem. Soc., 115, 91 (1993).
15. Asymmetric copolymerization of α-olefins and CO: a) M. Sperrle and G. Consiglio, J. Am. Chem. Soc., 117, 12130 (1995); b) Z. Jiang and A. Sen, J. Am. Chem. Soc., 117, 4455 (1995); c) S. Bronco, G. Consiglio, S. DiBenedetto, M. Fehr, F. Spindler, and A. Togni, Helv. Chim. Acta, 78, 883 (1995); d) M. Brookhart, M. I. Wabner, G. G. A. Balavoine, and H. A. Haddou, J. Am. Chem. Soc., 116, 3541 (1994); e) S. Bronco, Consiglio, R. Hutter, A. Batistini, and U. W. Suter, Macromolecules, 27, 4436 (1994);
16. Asymmetric copolymerization of α-olefins and CO: a) M. Sperrle and G. Consiglio, J. Am. Chem. Soc., 117, 12130 (1995); b) Z. Jiang and A. Sen, J. Am. Chem. Soc., 117, 4455 (1995); c) S. Bronco, G. Consiglio, S. DiBenedetto, M. Fehr, F. Spindler, and A. Togni, Helv. Chim. Acta, 78, 883 (1995); d) M. Brookhart, M. I. Wabner, G. G. A. Balavoine, and H. A. Haddou, J. Am. Chem. Soc., 116, 3541 (1994); e) S. Bronco, Consiglio, R. Hutter, A. Batistini, and U. W. Suter, Macromolecules, 27, 4436 (1994);
17. Asymmetric copolymerization of α-olefins and CO: a) M. Sperrle and G. Consiglio, J. Am. Chem. Soc., 117, 12130 (1995); b) Z. Jiang and A. Sen, J. Am. Chem. Soc., 117, 4455 (1995); c) S. Bronco, G. Consiglio, S. DiBenedetto, M. Fehr, F. Spindler, and A. Togni, Helv. Chim. Acta, 78, 883 (1995); d) M. Brookhart, M. I. Wabner, G. G. A. Balavoine, and H. A. Haddou, J. Am. Chem. Soc., 116, 3541 (1994); e) S. Bronco, Consiglio, R. Hutter, A. Batistini, and U. W. Suter, Macromolecules, 27, 4436 (1994);
18. Asymmetric copolymerization of α-olefins and CO: a) M. Sperrle and G. Consiglio, J. Am. Chem. Soc., 117, 12130 (1995); b) Z. Jiang and A. Sen, J. Am. Chem. Soc., 117, 4455 (1995); c) S. Bronco, G. Consiglio, S. DiBenedetto, M. Fehr, F. Spindler, and A. Togni, Helv. Chim. Acta, 78, 883 (1995); d) M. Brookhart, M. I. Wabner, G. G. A. Balavoine, and H. A. Haddou, J. Am. Chem. Soc., 116, 3541 (1994); e) S. Bronco, Consiglio, R. Hutter, A. Batistini, and U. W. Suter, Macromolecules, 27, 4436 (1994);
19. Asymmetric copolymerization of α-olefins and CO: a) M. Sperrle and G. Consiglio, J. Am. Chem. Soc., 117, 12130 (1995); b) Z. Jiang and A. Sen, J. Am. Chem. Soc., 117, 4455 (1995); c) S. Bronco, G. Consiglio, S. DiBenedetto, M. Fehr, F. Spindler, and A. Togni, Helv. Chim. Acta, 78, 883 (1995); d) M. Brookhart, M. I. Wabner, G. G. A. Balavoine, and H. A. Haddou, J. Am. Chem. Soc., 116, 3541 (1994); e) S. Bronco, Consiglio, R. Hutter, A. Batistini, and U. W. Suter, Macromolecules, 27, 4436 (1994);
20. f) Z. Jiang, G. S. E. Adams, and A. Sen. Macromolecules, 27, 2694 (1994).
21. N. Sakai, S. Mano, K. Nozaki, and H. Takaya, J. Am. Chem. Soc., 115, 7033 (1993).
22. K. Nozaki, N. Sato, and H. Takaya, J. Am. Chem. Soc., 117, 9911 (1995).
23. a) J. Tsuji and S. Hosaka, J. Polym. Sci., Part B: Polym. Lett., 3, 703 (1965);
24. b) A. Sen and T. W. Lai, J. Am. Chem. Soc., 104, 3520 (1982).
25. E. Drent, Eur. Patent Appl. Ep 229408, (1986); Chem. Abstr., 108, 6617 (1988).
26. D. J. Liaw, J. Polym. Sci., Part A: Polym. Chem., 31, 309 (1993).
27. E. Drent, Eur. Patent Appl. Ep 504985, (1992); Chem. Abstr., 118, 103023 (1993).
28. Asymmetric polymerization of 1,5-hexadiene was reported to give a polymer including cyclopentane in the main chain. See Ref. 5c.
29. Very recently, cyclocopolymerization of 1,5-hexadiene with carbon monoxide has been reported by using Shell-type catalyst, 1, 3-bis(diisopropylphosphino)propane-Pd(II). S. L. Borkowsky and R. M. Waymouth, Macromolecules, 29, 6377 (1996).
30. R. Giuliano, A. Ermili, and M. Artico, Ann. Chim. (Rome), 50, 1777 (1960).