Cobalt(III)-catalyzed cycloaddition polymerization of diynes with nitriles: Synthesis of polymers containing pyridine moieties in the main chain

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 37, Issue 13, 1999, Pages 1979-1986

  Lee, Jong Chan ^a   Tomita, Ikuyoshi ^a   Endo, Takeshi ^a  

^a Tokyo Institute of Technology ^*  (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; CATALYSIS; CATALYSTS; COBALT COMPOUNDS; MOLECULAR STRUCTURE; NITROGEN COMPOUNDS; ORGANOMETALLICS; POLYMERIZATION; SYNTHESIS (CHEMICAL);

CYCLOADDITION; DIYNES; NITRILE; PYRIDINE;

AROMATIC POLYMERS;

EID: 0032636106     PISSN: 0887624X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0518(19990701)37:13<1979::AID-POLA11>3.0.CO;2-I     Document Type: Article

References (19)

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2. Chauser, M. G.; Rodionov, Yu. M.; Cherkashin, M. I. J Macromol Sci, Chem 1977, 1113.
3. Yamamoto, T.; Mariyama, T.; Zhou, Z.-H.; Ito, T.; Fukuda, T.; Yoneda, Y.; Begum, F.; Ikeda, T.; Sasaki, S.; Takezoe, H.; Fukuda, A. J Am Chem Soc 1994, 116, 4832.
4. Tomita, I.; Lee, J.-C.; Endo, T. Macromolecules 1995, 28, 5688.
5. Tsuda et al. also reported the same type of pyridine-forming polymerization. See: Tsuda, T.; Maehara, H. Macromolecules 1996, 29, 4544.
6. Yamazaki, H.; Wakatsuki, Y. J Organomet Chem 1977, 139, 157.
7. Jhonson, M. D.; Tobe, M. L.; Wong, L. J Chem Soc A 1967, 491.
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9. (b) Aggour, Y. A.; Tomita, I.; Endo, T. Makromol Chem 1993, 194, 3323.
10. The Co-catalyzed pyridine-formation reaction of acetylenes with nitriles has been reported. See: (a) Wakatsuki, Y.; Yamazaki, H. Tetrahedron Lett 1973, 36, 3383.
11. (b) Wakatsuki, Y.; Yamazaki, H. J Chem Soc, Dalton Trans 1978, 1278.
12. (c) Wakatsuki, Y.; Nomura, O.; Kitaura, K.; Morokuma, K.; Yamazaki, H. J Am Chem Soc 1983, 105, 1907.
13. (d) Vollhart, K. P. C.; Bergman, R. G. J Am Chem Soc 1974, 96, 4996.
14. (e) Bonnemann, H.; Brinkman, R. Synthesis 1975, 600.
15. (f) Wakatsuki, Y.; Yamazaki, H. Synthesis 1976, 26.
16. Both nitriles and acetylenes bearing aromatic substituents coordinated to the cobalt as a third component probably contribute more to stabilize the cobaltacyclopentadiene intermediates in comparison with aliphatic ones by π-delocalization of the electrons of the substituents.
17. The formation of the monoacetylenecobalt complex is reported. See: Yamazaki, H.; Wakatsuki, Y. J Organomet Chem 1977, 139, 157.
18. 4-cyclobutadiene)cobalt at higher temperature to lose the catalytic activity. See: Yamazaki, H.; Hagihara, N. J Organomet Chem 1967, 7, 22.
19. As to discuss clearly the structure of 7Cc, the spectra of the model compounds (Figures 2b,c and 3a) were cited from our communication (in ref. 4) as a reference with slight modification.